Wholesome Crossdresser

He's just trying to help a friend.

Ed Wood: I like to dress in women's clothing.
George Weiss: You're a fruit?
Ed Wood: No, not at all. I love women. Wearing their clothes makes me feel closer to them.
George Weiss: You're not a fruit?
Ed Wood: No, I'm all man. I even fought in W.W.2. Of course, I was wearing women's undergarments under my uniform.

— Ed Wood

Crossdressing characters who are presented in a positive (or at least neutral) way. Frequently presented as attractive (or at least not unattractive), relatively "normal" people as opposed to perverts or sexual deviants.

The Wholesome Crossdresser may be of any sexual orientation, but in settings where being straight is considered part of being "normal", one can expect to see the character's heterosexuality explicitly highlighted.

Some permutations of the trope are more or less unique to Japanese works. The Japanese Wholesome Crossdresser is usually well-groomed, compassionate, nice, and above all, so convincing that their sex is only mentioned on occasion, as a reminder to newer members of the audience. There's a fair chance someone will get a crush on them, although this is usually resolved after The Reveal.

The opposite of Creepy Crossdresser. May overlap with Disguised in Drag or its Distaff Counterpart, Sweet Polly Oliver. (If the character wears cross-dressing disguises more often than seems strictly necessary, this trope may apply.) Wholesome Crossdressers tend to enjoy dressing, even if only reluctantly, secretly, or subconsciously.

Often overlaps with Drag Queen (a campy, hyper-feminine form of expression with heavy ties to gay/bi male culture), but usually doesn't with being Transgender (an intricate subject that is more connected with inward identity than outward appearance). However, if the character does this enough, then it may make fans think that they're trans.

Compare Otokonoko Genre, which is about male crossdressers (and occasionally Transgender women), that are almost always presented as wholesome. Contrast Embarrassingly Dresslike Outfit.

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Examples:

Anime & Manga

• Husky from +Anima is introduced in the series as a pretty Mermaid Princess. Later you find out the pretty pretty princess is actually a boy cross-dressing for cash. Later, after being kidnapped and sold as a slave in Sailand, he dresses up like a girl so he'll sell for a higher price. Cooro and Nana come to take him from his Master's home, and neither of them can tell that the fish + anima is actually Husky in a wig and girly clothes until they get right up in his face.
• From +C: Sword and Cornett, there's multiple instances of this; both Belca and Eco have had to cross-dress to escape the public eye, and while for the most part it's a disguise, it appears that yes, they're very much this trope. In his youth, Eco apparently went out to drag contests, and when he's hiding from guards after escaping the castle, Musca finds him and asks him to fix her hair, because she thought he was a "pretty lady". Belca, dressed a girl (though he's wholely unwilling), accidentally has someone fall in love with him, and Musca's likewise called him a pretty lady. Eco says himself that Belca makes for a pretty girl — not a pretty as himself, of course.
• Noto Kanazawa aka Noto-sama, the star of the short manga Advance Kitakou Broadcasting Club by Hidekaz Himaruya. He's a cross-dressing School Newspaper Newshound who's often found stripping other people with his partner-in-crime, Yamato Nara from another Himaruya comic, Barjona Bombers.
  • It should be noticed that the Noto in the early Kitakou stories is virtually a completely different character. He isn't a WSC, just an Ordinary High-School Student and a bit of a Butt-Monkey, as well as being much less pushy. After the series added Pure to its title and Himaruya started drawing Barjona, Noto was revealed to be Cute and Psycho and snapped, starting on the path to his current incarnation. This era of the comic was taken off the website though, presumably due to Old Shame.
  • Koedo Chiba, a minor character in the Pure part of the series, is both this and a Bokukko. Due to having been made fun of as a child for looking like a boy, she opted to actually live her life as one.
• Minoru in AKB49 – Renai Kinshi Jourei crossdresses to join an all-girl idol group to watch over his crush who is in the same group and protect her dream, without her knowledge.
• Sister from Arakawa Under the Bridge. The man wears a nun's habit for day-to-day life and on one occasion donned a schoolgirl uniform.
• Astro Boy examples:
  • Astro disguised himself as his sister Uran in "The Greatest Robot in the World" (Tetsuwan Atom, 1963), which likely makes him anime's first crossdresser.
  • In the original manga story and the 1980s anime, Uran disguised herself as Atom/Astro so she could fight Pluto in his place.
• In Basquash!, Princess Flora Skybloom takes off to the city, to watch the protagonist's development close-up. To hide the fact that she's royalty, she disguises herself as a boy, hiding her hair beneath a baseball cap and taking on the name Alan Naismith. She does a pretty good job of disguising it, too, except that she was unable to restrain her love for the extremely girly Idol Band, Eclipse.
• Beastars: Legoshi has twice dressed in women’s clothing while at the Black Market. The first time he does it was to disguise himself from the Shishigumi, one of the four major criminal gangs who he had just rescued Haru from, to talk to Louis, who had just become the head of the gang after killing the previous head, about Riz. The second time was when he decided to face all four criminal gangs previously mentioned, with a problem arising from the fact that one of them, being the Inarigumi, is made up of all-women and he Wouldn't Hit a Girl, Legoshi being a Cloudcuckoolander decides to get around this by dressing up as a girl.
• Black Butler:
  • Ciel in episode 4 of the anime, he sneaks into a ball in a very... special outfit◊. Keep in mind that he's a twelve-year-old boy who runs his own company. This outfit is famous in the series, to the point of where it even has its own fanbase and cosplay design. Heck, it's much more famous and recognized than even his regular clothes. It's really saying something when, by searching the term "Ciel Phantomhive" in Google Images, 99% of the pictures that pop up are of him in that outfit. Anyone who didn't know the series would probably be under the impression that he is a she.
  • Alois Trancy in the non-canon Season 2 forces his maid Hannah to dress him in her clothes and puts on a wig in order to get closer to Ciel. It does not work as Ciel sees right through the disguise.
  • Sieglinde Sullivan does it, too. Even before she has to swap clothes with Ciel as a disguise, when she wishes to wear clothes from the "outside world" and Sebastian tells her Ciel's are the only clothes her size available, she's more than okay with it (it's her staff who won't let her). Though in Sieglinde's case, she probably simply doesn't care as long as it's something different.
• In the Black Cat anime, both Train and Sven are shown crossdressing. For Sven, he wears a very frilly, fancy dress to try to lure a killer for a bounty. It doesn't work. For Train, after transforming into a child, while Eve and Kyoko go out to buy clothes the right size for him, he's forced to wear Eve's dress.
• Hideri Kanzaki of Blend-S is a boy who dresses like a girl. He works as a waitress at a cafe and desires to be the cutest. Unlike most examples, he's more similar to a Real Life transvestite — he does that because he likes it, yet he continues to see himself as male and appears to be heterosexual.
• The short-lived Blue Wars manga provides an odd example with the Sera brothers. Yuuri Sera has always looked and acted exactly like a lovely young girl and is consistently treated as such by "his" family and friends. "His" younger brother, our protagonist Ryousuke, would like to do the same but, by virtue of being more muscular and manly in appearance, is stuck to manly standards as heir of their father's dojo. The plot is driven by how he tries to get around this.
  • Another, sadder, example is Suguru who is perfectly happy being gay man living with his partner. However, he starts to grow out his hair and crossdress as a woman once his adopted son starts to get bullied in school for having two dads.
• Nakahara Tatsuki from Boku No Tsukuru Sekai, a Magical Projectionist teacher and Ritsuki's father, as revealed by the latter by calling him "Dad" in Volume 1, p. 8. His reasoning for his appearance is that he "is a professional Projectionist! I walk the fine line between the genders so as to not give anyone any strange preconceptions" (Volume 1, p. 8).
• Ryo Hayama of Bremen fully dresses up as a girl which includes wigs, fake boobs, platform shoes, fake nails, etc. Just beware about calling him one.
• Butterflies, Flowers: Domoto's coworker and very close friend Suou, of whom Choko is quite jealous until she realizes he's a he.
• ChocoMimi has Mumu, who often wears girl's clothing and frequently brags about how cute he looks in it. Sometimes he tries to exploit this cuteness, such as the Beach Episode where he dresses as a cute girl to get free food from a vendor.
• The whole shtick of Chotto Edo Made is about a girl who dresses like a boy and her love interest, a boy who dresses and acts cutesy like a girl (with eyelashes to boot).
• Code Geass Picture Dramas featured Rivalz, Suzaku and Lelouch crossdressing as girls. Suzaku doesn't seem to mind while Lelouch, who is prettier in a fancy dress, didn't like it and gets harassed by Suzaku and Rialz on Student Council President Milly Ashford's orders. The R2 picture drama has him dressed up as a belly dancer of all things so that he, Kallen and C.C. can infiltrate the Chinese Federation's territory. The PSP Visual Novel game, Lost Colors, has the Player Character, Rai, having an Imagine Spot of Lelouch wearing a wedding dress and boy, he still looks pretty.
• A number of transvestites appeared in "Jupiter Jazz", an episode of Cowboy Bebop. One of them even returned for The Movie.
• Crimson Spell has Prince Vald, a sweet, idealistic Knight in Shining Armor who frequently cross-dressed as a child to hide his status as the heir to a country at war. When he needs to get into a party without being recognized, he opts to dress as a girl again, and he's so successful that even his own Love Interest doesn't spot him. Afterwards, when he's stuck in his demon form for unrelated reasons, his friends joke that it's because he's pissed they made him take off the dress.
• Hans of The Daughter of Twenty Faces does this, albeit unwillingly, for a circus act the nakama are producing in episode 5 of the anime.
• Kei does this in the intro sequence of Dirty Pair during a sepia-toned clip of her chasing some mustachioed men in fedoras, briefly removing her fedora and fake moustache to mug for the camera.
• Seki from Doki Doki School Hours likes to dress up in women's attire - actually hoping he will impress girls that way.
• Excuse Me Dentist, It's Touching Me!: Tomori crossdresses for a few reasons: he finds it fun, he thinks he looks nice when doing so, and it makes it easier to have a life outside of the Yakuza, and he's overall a very nice man outside of his insensitivity when talking and snarky tendencies, and the sanest person in the cast.
• Eyeshield 21 had Ootawara and Sakuraba dressed as maids (during a public practice) as a punishment for losing a trivia game during a school festival. This, however, only increased Sakuraba's popularity. Hiruma also dressed like a maid to spy on the players from the American team. Panther got a good laugh out of it.
• In Fairy Tail, after the Council orders the arrest of Erza (after the incident involving Lullaby and the sheer amount of collateral damage it caused), Natsu decides to break into the trial dressed as her and admitting guilt, so as to get her off the hook. Needless to say, the real Erza is mortified. In the end, it was just a mock trial so that the Council could assert their authority. They were going to let Erza off anyway, but thanks to Natsu, both wound up getting really arrested.
• Fruits Basket features several wholesome crossdressers:
  • Among the men of the Sohma family: Ritsu always wears women's clothing out of insecurity and Ayame is an equal-opportunity sort who runs a fetish costume shop. Momiji is more of a downplayed example, since his casual outfits tend to skew feminine but he always wears shorts instead of skirts or dresses.
  • Subverted in the case of Akito: shortly after we learn they are a Creepy Crossdresser, they turn into the wholesome variety (eventually they stop and accept themselves as their original gender).
• In Fullmetal Alchemist, there's an automail engineer named Mr. Garfiel. Though initially he doesn't wear female clothes, only makeup, he puts on some lacy, poofy shirts later on. He also acts overly feminine, even compared with the manga's normal female cast. He also frequently flirts with Ed and other male characters.
• Fushigi Yuugi:
  • Chou Ryuuen aka Nuriko. His actual gender is revealed pretty early on in the series.
  • Bishounen Hotohori, while usually just mistaken to be a woman (especially by Miaka during their first meeting), with minimal effort he has on occasion been a Wholesome Crossdresser . He had to enamor a band of thugs by pouring drinks for them (he only had to powder his face) and in the manga when he, Miaka and the Suzaku Seishi visited a females-only public bath where all of the males were temporarily Wholesome Crossdressers (he and Nuriko were the only men convincingly looking like women, to the chagrin of the others).
• Used as a one-off gag in Game×Rush, where the middle-class Memori is portrayed as a "Cinderella" as opposed to Yuuki's imagined wealth. Also, Memori dresses as a nurse to "avoid suspicion" and stay in the hospital after hours... to make sure Yuuki doesn't escape, of course.
• Yellow Belmont from Genesis Climber MOSPEADA (Lancer/Yellow Dancer in Robotech).
• Genshiken:
  • Kousaka crossdresses to help the club sell doujinshi at a comic festival. His club mates find it surprisingly convincing.
  • Genshiken Nidaime introduces Hato Kenjirou, who crossdresses as a way of life, and never visits the club as a boy.
• Kazuki in Get Backers. The writers, especially in the anime, will take any excuse they can to get him into women's clothing. Sometimes it's a misunderstanding, sometimes it's part of his job, sometimes it's favor for a friend... and then there's the official art of him in women's swimsuits. The anime went so far as to lampshade it in the fourth ending: there are two points where the characters are divided by gender, and he's with the girls both times. To be fair, he's mistaken for a woman when he's not explicitly crossdressing.
• Gintama has the Okama bar that created the lovely Paako and Zurako. Gintoki, Shinpachi and even Kagura have no problems crossdressing when they need to...or just for the hell of it, actually. And there's also Yagyuu Kyuubei.
• Girls Saurus has a weird case with Tsubasa, who is male (and heterosexual) but so pretty and effeminate that a lot of people straight up visualize him as a girl. He attends an all-boys school and relishes spending time in a masculine environment... entirely unaware that every single classmate of his are convinced he's a girl masquerading as a boy. They also find the whole concept so romantic that they've all sworn not to reveal 'her' secret, and avert their eyes when they change for P.E., which is how the whole absurd deal is kept going for so long. Tsubasa is, suffice to say, very upset to learn all this.
• Racine Blanche Volban in Glass Fleet assumes her brother Michel's identity after his death in battle, and passes herself off as a man thereafter. In the process she also acquires her brother's Stalker with a Crush, who is a bit put out when he discovers that "Michel" is a woman.
• Eiji Shigure in Gravion, while not a crossdresser by custom, ends up disguised (or at least dressed) like a woman quite a few times over the course of the series with little to no complaint. Then towards the end of the series, we find out that Sandman's Battle Butler was Eiji's missing sister the whole time, so it seems to run in the family.
• Gundam examples:
  • Loran Cehack's female alter-ego Laura Rolla in ∀ Gundam. It's forced onto him by Guin intentionally reporting that the Gundam pilot is a woman, and the reason why is because Guin has an unhealthy lust for him. Despite Loran being straight.
  • In a possible homage to Laura Rolla, Gundam 00's Tieria Erde dons a dress, long hair extensions, and a large set of fake breasts at one point in the second season. Why? So that he can sneak into a high class party and speak to Ribbons. And to make fangirls melt into a collective puddle over Stupid Sexy Girl!Tieria, while several fanboys went "TIERIA IS A MAN AND HE'S OURS!".
• Iori Akizakura, one of the protagonists of Handsome Girl and Crossdressing Boy He first does it after losing a bet, but finds out he likes it.
• Huo Long from Haou Airen. His heart is in the right place, but he is a Triad member.
• In several episodes of Hayate the Combat Butler, poor Hayate is forced by Nagi to crossdress in blatantly female costumes like sailor fuku or a catgirl costume. The fact that Hayate's physical and facial features are sexually ambiguous mean that some of the male characters may get the wrong idea... Hayate's tendency to act Moe in these types of situations doesn't help, either.
  • It's so wholesome that he actually has a male over the top in love with him. He ends up crushed when Hayate is exposed as a man...for all of half of chapter before turning "It's okay if it's you".
  • Its even worse in the manga: Ruka first meets Hayate when he is crossdressed (long story). When she later sees him in his butler uniform, she asks if he's a girl who likes to wear boys clothes. How well Hayate fits here is even a bit of a Running Gag in the manga.
• Makoto Mizuhara from El-Hazard: The Magnificent World, Yakumo from 3×3 Eyes and Yellow Belmont aka Lancer from Genesis Climber MOSPEADA/Robotech Third Generation crossdress as a plot necessity rather than for their personal tastes. I.e.: Lancer crossdresses and poses as a female Idol Singer to act as a spy for the resistance group he's a part of, Makoto was Disguised in Drag posing as the missing Princess Fatora, and Yakumo crossdressed for his night job.
• Itsuki of HeartCatch Pretty Cure! spends half of the series dressed up as a guy and is usually seen in her male school uniform, mostly because she's determined to take over her grandfather's dojo while her older brother is sick. However, once her brother is cured and she takes up the role of the third Precure, she starts sliding back into more feminine roles, becoming a member of Erika and Tsubomi's fashion club and is seen in the Distant Finale wearing the school's female school uniform.
• A running joke in Here is Greenwood is Shun being mistaken for a girl. His younger brother is likewise androgynous enough to be distracting.
• The titular Hikaru from Hikaru to Hikari definitely qualifies, especially if the crushes Yuuto and Sumitane have on his alter ego "Hikari" are any indication.
• Azami in Himawari! is a male spy at an all-girls' ninja school, and wears the appropriate clothing. Everyone knows he's a guy and doesn't mind, because the whole spy thing means inside info for both sides.
• Hime, from Himegoto, is forced to dress as a girl during school. In the spinoff Himegoto+, everyone in the main cast cross-dresses.
• Mayotama from I Can't Understand What My Husband Is Saying has a very feminine build, enough for Kaoru and Miki to confuse him for Hajime's younger sister rather than his brother. He also holds his arms as if he was a woman covering her breasts when he's in a hot spring.
• Hibiki-sensei in I My Me! Strawberry Eggs, who cross-dresses in order to get a job from a man-hating boss. His Mentor is also a transvestite whose failed marriage to the boss caused her man-hating.
• Kei from IRIA: Zeiram the Animation.
• Hiura Mihate of I Think I Turned My Childhood Friend Into a Girl jumps headlong into wearing girls' clothing after his childhood friend first applies makeup on him.
• JoJo's Bizarre Adventure:
  • Subverted in one chapter of Battle Tendency, where Joseph cross-dresses as a tequila girl for a disguise to fool the Nazis. He fails to realize that most women aren't quite as well-built as he is. Hilarity Ensues.
  • In a slightly more feminine example, Narciso Anasui from Stone Ocean is a very effeminate-looking crossdresser, although the "wholesome" part is highly up for debate here. While he is one of the good guys and seems to be genuinely in love (although his courtship methods are... strange, to say the least) with the main character, Jolyne, he is also an insane killer who has an obsession with taking objects and people (including his old girlfriend and the man she was caught cheating with) apart. He may even fall under Creepy Crossdresser, depending on who you ask. His appearance becomes much less feminine over time, with him pretty much being fully masculinized by the end of Stone Ocean (other than the women's clothes, of course).
  • In JoJolion, it is tradition for the first-born sons of the Higashikata family to crossdress until they are 12. This is done as a way to ward off a curse that turns all firstborn sons of the family to stone. The current child doing this, Tsurugi, doesn't seem to mind.
  • The deuteragonist of The JOJOLands, Jodio Joestar's older brother Dragona Joestar, is an exceedingly effective crossdresser, with him looking exactly like a woman, wearing bikinis and women's clothing, and even receiving breast implants. He is a drug-trafficking criminal like his younger brother, but unlike Jodio, who's unscrupulous and egotistical, Dragona is very affable and always knows when his little brother is going too far.
• Kaguya-sama: Love Is War:
  • The cheer team crossdresses as part of their performance at the sports festival. Ishigami (who had joined in the hopes that it would make him happier and more social), ends up borrowing Kaguya's uniform for the event, and the scene where she has him try it on to see if it fits is the first real moment of what would become an incredibly wholesome sibling-like bond between the two.
  • Implied with Kogane Kanegae from the new student council at the end of the series. He identifies as a genderqueer male but wears the female Shuchi'in uniform, and it's never made clear if he's doing it by choice or if he's forced to due to having been assigned female at birth.
• Izumo Kunisaki from, well, Kunisaki Izumo no Jijou, who is already attractive enough to be mistaken as a girl all the time, frequently cross-dresses as a result of him invariably receiving female roles from his family's kabuki troupe, much to his chagrin. His senior in the troupe, Kagato, is another one, although unlike Izumo he actually enjoys it.
• Level E: During the RPG Episode, prince Baka cast himself in the role of the distressed princess, and disguise accordingly. Later in the same episode we see him dressed as a Dominatrix, a school girl and a teacher.
• Love Me For Who I Am: Suzu and Ten are cis men but still enjoy cross-dressing both at the Maid Cafe and in their personal lives when possible. Both put in a lot of effort into looking feminine and are equally as attractive as their other co-workers when in their uniforms.
• Alto Saotome from Macross Frontier used to be a Kabuki actor who specialized in female roles before he became a pilot. As a result, he retains a very feminine look even when wearing male clothing. This is Lampshaded by his friends, who often tease him and call him "Princess Alto" due to his appearance. People who don't know Alto will sometimes mistake him for a girl. It doesn't really help when some fans admit that they find Alto hotter and more attractive than his own mother. Taken to a higher level in the second movie where Also dresses up as a maid.
• Maid-Sama!:
  • Yukimura as well, although in his case it's a matter of periodically being forced to crossdress (very convincingly) by the other characters rather than doing it of his own initiative. You can have three guesses as to what kind of aura other characters feel from him (despite his best efforts) and the first two don't count.
• Shizu in Maria†Holic. Of course, she only crossdresses when attending classes (she and her brother are in a competition with each other, and part of the competition involves attending both a boys' school and a girls' school during their high school years).
• Miyashita Masashi from Me & My Brothers. His official reason for this is due to his profession as a romance novelist, whose demographic for his novels is women. Masashi constantly crossdresses and Cosplays as a means of better understanding the female mind and applying this knowledge to write successful stories. The real motivation is possibly revealed in the last chapter of the manga, where in junior high, while Sakura is about three years old and Masashi about fourteen, he had to dress as a junior high school girl for a student-run film project, much to Masashi's chagrin. Later, he admits that Sakura enjoys it when he dresses femininely, so it might not be such a bad thing after all.
• An episode of Michiko & Hatchin had Hatchin meeting a man whose job involves him being a cross-dressing actor. While he wears men's clothes outside of work, his son dresses as a girl 24/7 and wants to be a female impersonator like his father when he grows up.
• Midori Days:
  • Seiji is forced to crossdress in an attempt to catch a molester on a train. Naturally, some acquaintances from school see him, and decide that he's hot.
  • Kouta is often forced to wear various female outfits by a female gang in the manga.
• Makoto/"Mako-chan" in Minami-ke. All it seems to take is a hair clip and a skirt and bam! Uncannily cute & convincing girl. Like, "make you doubt your own preference" convincing. Interestingly, his first comment in the second season is being glad he can dress normally again... only for Kana to take one look at "normal" Makoto and shut the door in his face. Cut to him in a girl's outfit, with the comment the girls can't accept him otherwise.
• Ilulu from Miss Kobayashi's Dragon Maid wears a men's outfit when at work due to the fact that there aren't any women's clothes that would fit her proportions. This comes up again in a chapter of Kanna's Daily Life when she tries on some school uniforms and finds the Sailor Fuku too constricting, while the boy's uniforms fit just fine.
• Monthly Girls' Nozaki-kun: Tsubaki has an overall positive/light-hearted approach to characters wearing clothes typically worn by the opposite sex, as part of her gender-role-defying ways.
  • There's often official manga art of the male characters wearing dresses/skirts which are all done for fun rather than mockery: for example, the Nozaki brothers and Mikoshiba are in frilly dresses as a tarot card (with only Mikoshiba looking confused), and Nozaki happily wears a similarly frilly dress on the Chapter 87 cover.
  • Nozaki willingly tries on the sailor uniform for manga purposes when Sakura refuses to model it for him, and even gets upset because his muscles stop it from fitting him properly. He also considers wearing a custom-made sailor uniform for a fansign to portray his image as a female shoujo manga author.
  • Kashima encourages Hori to pursue his (nonexistent) "princess" dreams by giving him girls clothes to wear. He doesn't quite appreciate her "kindness" (but is still impressed by the outfit coordination). Tsubaki implies in the fanbook Hori would eagerly play the princess opposite Kashima in order to keep her and would go as far as to wear a corset to look the part. And when Rei asks him if he looks good in ladies' clothing (to see if he complements her Bifauxnen sister), he seriously considers the idea before stopping himself.
  • Bifauxnen Kashima herself, of course, happily wears her "bookish male student" fashion when she's not in her prince costume or waiter uniform (or the two times she got away with wearing the school pants).
  • Sakura's brother Towa seems to think Kashima in her normal girls' school uniform itself is her crossdressing. He mistakes her for the "model" Nozaki and concludes "he" wears the skirt because it's the trend, which Towa finds cool. He finds out she isn't Nozaki but not that she's a girl.
• In the My-Otome manga, Princess Mashiro is replaced by her twin brother. The gags of the manga constantly poke fun at "Manshiro's" plight.
• Subaru Shiratori of Nameless Asterism is a boy who periodically cross-dresses. He typically borrows his twin sister's clothes to do so.
• Naruto:
  • Haku is on the borderline between Wholesome Crossdresser and Creepy Crossdresser being that he's an Anti-Villain.
  • From the fillers, there's Princess Toki of the Land of Birds, who is also impersonating her dead brother Sagi.
• Cruz, from NEEDLESS, unwillingly dresses as a girl in the later part of the manga (and ended up popular with his teammates as well as the readers) in order to survive at an all-girls Academy. The academy uniform becomes his default outfit for the rest of the series, initially because his original clothes were thrown away, and then gets a bounty on his head and has to remain cross-dressing to avoid attention from his enemies, and later just because his companions shoot down the idea of wearing boys' clothes again when he brings it up. As of manga chapter 113, Cruz is officially changed into a female by Blade's godly powers, to the amusement of the majority of his companions.
• Negima! Magister Negi Magi:
  • The series combines this with Instant Cosplay Surprise, with the girls dressing Negi up as a surprisingly cute fox girl. It sure gave Ayaka a massive nosebleed.
  • Negima?! Neo has Cheerleader Negi in chapter 19. As seen here, he's not the only one in drag (hint: the other one's wearing bandages around her chest).◊
• Neon Genesis Evangelion's main character Shinji Ikari has crossdressed on two occasions, once wearing Asuka's spare plugsuit (complete with breastplates) and again when he and Asuka are training to defeat Israfel they wear identical ... "jazzercise" outfits. In Shinji Ikari Raising Project, Asuka and Rei find him even more attractive when he is forced to wear a dress. Do they get a bonus point for Les Yay?
• Kiri in the manga Never Give Up inherited her father's facial features and build and has a tendency to act "princely" on occasion, but has a distinctly female personality and wears the girl uniform. Doesn't stop half the school's female population from developing huge crushes on her. However, in order to stay close to her love interest, the effeminate Tohya, she has to sign a modeling contract. As a male model.
• Makoto in Nicoichi crossdresses to act the mother role for his son, who due to his young age could not understand the fact that his mother has already passed on.
• Yuki Nomura from the manga No Bra is a sweet, kind, beautiful and roommate Masato Kataoka's perfect girl. Except she's a he.
• Nononono is a ski-jumping manga by the author of Elfen Lied. The heroine Nonomiya is cross-dressing and passing for her dead twin brother because only men are allowed in professional ski-jumping... and she wants to win Olympic gold. Played very seriously.
• In Oh! Edo Rocket the reason for Genzo's cross-dressing is never explained, but it might be an attempt to get people to notice him. Though his hair and makeup are very feminine from the beginning, he doesn't actually dress in women's clothes until near the end of the series after his mother has sold all his clothes and the only thing left for him to wear is a dress. The reactions to this are overwhelmingly positive, and he then goes on to play the female lead, Princess Moonbeam, in a play that sums up the events of the series.
  His Mom: Could this gorgeous woman be my son?
  O-Nui: So pretty! Sweet, I'm so gonna take him viral!
  Oise: What a beautiful woman.... Darling, I have to ask, do you ever see yourself on stage?
• Ayase from Okane ga Nai is already mistaken for a girl when he dresses normally, in the manga he dresses up as a girl at one point thus becoming virtually impossible to be identified as male. In his case it might not be all that surprising that this earns him a severe stalker who is not bothered to learn his real gender and proceeds to stalk him anyway.
• One Piece has a number of examples:
  • The Kamabakka Kingdom is, quite literally, "full of transvestites". Even the animals are into it. While they may be portrayed as nice people, they're also pictured to be rather unattractive Brawn Hildas twice the size of an average human. There are also quite a few jokes about them Squicking out Sanji, as he was humiliated and forced into becoming a crossdresser himself for a period of time. However, they helped Sanji greatly with his training over the two-year Time Skip and he gained a great deal of respect for them.
  • Izo, commander of the 16th division of the Whitebeard Pirates is probably the best example of this trope, as he is maybe the only crossdresser who can't be spotted as one at first sight.
  • Mr. 2 Bon Clay. His fighting style is even called "Okama Kenpo" (Transvetite Fist Way), and he has no female partner in Baroque Works because "he counts as a man and a woman". As for the wholesome part, he is a firm believer in The Power of Friendship, a close friend of Luffy after his Heel–Face Turn, and pulled two Heroic Sacrifices to get him and the Straw Hats out of sticky situations.
• Ouran High School Host Club:
  • Ouran subverts this fairly well. Haruhi is mistaken for a male by the host club at first due to her grubby and vaguely masculine clothing. However, Haruhi never bothers to correct them until they find out and doesn't have any problems with people mistaking her for a male. She simply has a wide concept of gender and doesn't mind dressing in a variety of costumes of both genders.
  • Her father Ryouji (aka Ranka) is a slightly more traditional Wholesome Crossdresser, who works at an okama bar. At one point he violently shoots down Tamaki's idea that the club crossdress to get into Lobelia School, since 'amateur cross-dressing' is an insult to the profession.
• Both of the leads of Penguin Revolution are Wholesome Crossdressers. Ryo Katsuragi is obliged by his (rather quirky) talent agency to attend school as "Ryoko," and after she learns his secret and agrees to help him by acting as his personal agent, Yukari Fujimaru is obliged to dress as a man since the agency doesn't employ women as agents. Hilarity Ensues.
• Like her video game counterpart, Naoto Shirogane of Persona 4: The Animation is one of these.
• Anna Graham of Phi-Brain: Puzzle of God is an extremely girly boy, to the point that Daimon Kaito's childhood friend Nonoha starts to worry whenever Anna and Kaito are alone together, even after discovering his real gender. As for the "wholesome" part, Anna is a very friendly, sensitive artist, as well as a Friend to All Living Things.
• Pokémon: The Series:
  • Ash has to dress as "Ashley" to get his Gym battle with Erika. Brock is fooled, but Pikachu isn't (scent, maybe?). Ash would go on to invoke once a saga (minus Johto), once as a Meido.
  • Later in Unova he needs to set straight some snobby b's that bad-mouthed his Snivy from a female-only circus. Cue Ashley. Cilan was also caught in the crossfire because Iris was the actual instigator.
  • The tradition was (briefly) broken in XY when it was Serena who disguised herself as Ash while he was sick. Many fans felt robbed by this. Fortunately, the next season made up for it...
  • In Alola, when he and his classmates are taking over from a sick Joy, the guys failed to find the male uniform at first. Ash was pondering at getting away with the female uniform, but that sparked interest in the girls. With a dash of makeup and Rotom's blond wig, we get our cutest Ashley ever.
  • Many of James' disguises involve wearing dresses, even when there's absolutely no reason to (once he and Jessie posed as a bride and groom- him as the bride and her as the groom). One of James' disguises involves him wearing fake breasts for a beauty contest, which got an episode of the series banned. Jessie also used to crossdress a lot as well.
  • A few canonically male Pokémon have been shown in female clothing. Some of them are embarrassed but some, like Dawn's Piplup (who frequently cheered in a pink cheerleader outfit, though he also had a male kimono), aren't phased. An Unova episode even has Pikachu Disguised in Drag by taping a heart-shape onto his tail (the earlier-mentioned return of Ashley in Unova).
• Randoh/Yuna from Pretty Face. Justified/handwaved in that he was surgically rebuilt from a disfigured near-corpse to look like a teenaged girl.
• Princess Jellyfish features Kuranosuke, the main male lead of the series. He likes to dress up in women's clothing for the sake of it. Since the residents aren't fond of men, dressing up as a woman is his only way to keep visiting Tsukimi, whom he seems to be developing feelings for.
• The entire premise of Princess Princess is about pretty boys dressing up as "princesses" to provide refreshment for the other students of the all-boys school.
• Aikawa of Prunus Girl is very convincing, but helpfully reminds everyone at least once a chapter that he's a guy in between teasing Maki and hinting at Recursive Crossdressing.
• Ranma ½:
  • Tsubasa Kurenai, who's in love with Ukyō Kuonji, a Bifauxnen female crossdresser. A later character, Konatsu, also falls into Ukyō's orbit. It should be noted that Konatsu appears as a traditional Japanese kunoichi or female ninja. Of course, Konatsu was reared to think of himself as a girl (even covering his bare chest and squealing) with very few concessions to his masculinity. Tsubasa, on the other hand, is a Master of Disguise who can be anything from a mailbox to a tree... but he prefers to wear a schoolgirl uniform underneath, rationalizing that if Ukyō chooses to dress like a man, then he should dress like a girl to match. Note that both characters were wholly mistaken for female until the very last page of their introduction stories, although they never actually claimed to be girls. Although, in Tsubasa's case, his appearance was so convincing that, unaware that Ukyō had met him while going to a boys only school to further her own "masquerade", they initially believed him to be a girl who had mistaken Bifauxnen Ukyō for a real boy. Then they thought that "she" was a lesbian after they learned he had known Ukyō was really a girl all along (which greatly startled Ukyō herself, who had evidently figured that Tsubasa was a cross-dressing homosexual guy who had been fooled by her disguise).
  • Later in the manga, Ranma, Ryōga, and a couple other characters must distract the Yamata No Orochi, which has a taste for women. Therefore, they (as men, even Ranma) dress up as female stereotypes: a schoolgirl, a nurse, a meter maid, and a bride. Akane, meanwhile, crossdresses as a man to avoid being eaten.
  • Also a special note is to be made of Ranma him/herself. Although the Chinese uniform he tends to wear is generally thought of as genderless, he will often end up being turned back to male while wearing feminine attire (much to his chagrin and ridicule). On the other hand, standalone character illustrations, cover art, and chapter breaks tend to depict female Ranma as unusually feminine. However it depends whether or not it consider cross-dressing since through magic, Ranma can be completely biologically female or male at anytime. Either way he does seem to spend a lot more time being a woman than strictly necessary, and several gags are made out of him willingly dressing up in some very effeminate clothes and seemingly enjoying it.
• Revolutionary Girl Utena's Utena Tenjou is a girl-dressed-as-a-boy example. Her choice of attire doesn't really do anything to hide her femininity, though, being more a matter of preference due to her desire of one day becoming a Prince Charming.
• Oscar from The Rose of Versailles is another example of the girl-raised-as-a-boy plot device.
• Sailor Moon:
  • Usagi herself does this in the anime episode "Cruise Blues" when she sneaks onto a cruise ship disguised as a handsome young freelance journalist.
  • Haruka Tenoh often dresses as a man and many people mistake her for one. Notably, in the manga Haruka wore both men and women's clothing, while in the anime she almost exclusively wears men's clothing. Her proclivity for wearing men's clothing is never treated negatively, apart from some Unsettling Gender-Reveal after Usagi and Makoto crush on her and it's revealed she's a woman.
  • In the manga, the Starlights qualify, as they are women who disguise themselves as a boy band. Averted in the anime, where the Starlights have a biologically male disguise and transform into women when they take on their sailor forms.
• Gowther from The Seven Deadly Sins, kind of by design. He's an Artificial Human designed to look like the dead lover of his creator (the original Gowther), but male so as to avoid inapproriateness. Still, his design already lends him to having effeminate traits. After being forced to dress as a maid, Gowther found he liked it and adopted the trope. Other times, he may skirt it by dressing in gender-ambiguous clothing. Doesn't help that among the titular group, his designation is the Goat's Sin of Lust.
• Sgt. Frog: All five Keronians have crossdressed at least once, with Keroro himself as the biggest repeat offender. On the flipside, Kululu's debut episode has him turning Aki back into a 14-year-old — whereupon she dresses up in her son Fuyuki's school uniform and sneaks off to his school. Their resemblance is uncanny.
• Ayumi, in Shion no Ou, cross-dresses throughout most of the anime, in order to enter tournaments.
• Shugo Chara! has Nadeshiko; her relatives explaining this is a technicality of her family's dance career. The only two hints at this is her transformation is into a polearm-wielding maniac, similar to Tadase's ironic change, and not swimming. Interestingly, she is Put on a Bus before anyone but the audience finds out (Amu is just smitten with her 'twin brother' for the day) though seems amused when she thinks how she'll officially explain it to Amu when she returns.
  • Interestingly, at this point there's more than a few gags that the show was becoming a Cast Full of Pretty Boys in regards to the 'normal characters', with her Chara teasing Amu's habit of crushing on every - one.
• In There, Beyond the Beyond, Futaba admits that wearing girly clothes doesn't bother him, because his older sister makes him do it all the time.
• In Tokyo Ghoul :Re, several characters crossdress as part of an investigation into a human trafficking ring targeting young women. Sasaki not only looks stunning in disguise, but is shown really enjoying getting into the role of "Sasako". When a superior later criticizes his "unconventional" methods, it further establishes him as a Jerkass and completely unreasonable. During the same investigation, Suzuya epically puts a stop to a slave auction while wearing a long wig and Lolita dress.
• Transformers: Cybertron: Part of Override's bio from her toy (only available after entering her Cyber Key code on the TFC website) states that in order to win leadership of Speed Planet she entered the race disguised as a male. Exactly how this works (or for that matter why she'd do it) isn't mentioned.
  • It was meant as a Mythology Gag referencing the fact that in the original Japanese, she's already male.
• Fay in Tsubasa -RESERVoir CHRoNiCLE- sometimes does this. In the Alternate Universe Omake first Drama CD, he is shown wanting to join the girls as they dressed in maid outfits for the school festival, and in a strip comic for New Year's he wore a female kimono borrowed from Yuuko. He comments that he did it in secret because Kurogane hadn't let him wear the maid costume.
  • Also, in the main storyline, he consistently wears a furisode ^note usually reserved for unmarried women and, traditionally, gay lovers whenever he wears kimono. This includes the gang's stay in Japan, as well as the cover art of a couple of chapters. Unlike in Horitsuba Gakuen, the kimonos he wears in Tsubasa -RESERVoir CHRoNiCLE- are worn in a masculine fashion; however, they are identifiable as furisodes due to the sleeve length.
• Kotarou from Ultimate Otaku Teacher is so feminine that he was banned from wearing the male uniform.
• Unico the Baby Unicorn from the Unico series is occasionally seen wearing pink or yellow◊ eyeliner around his face. While the protagonist doesn't dress in female clothing in the actual series. Osamu Tezuka would occasionally depict him wearing a red bow around his horn◊ in numerous illustrations.◊ Unico actually enjoys dressing up in female makeup, and is brifely seen wearing a red ribbon around his tail during the prologue for the 1981 animated film The Fantastic Adventures of Unico (which was lifted from the manga) alongside using a mirror to check his physical appearance.
• Nagisa and Ryunosuke from Urusei Yatsura, a boy and girl who are forced to crossdress by their fathers and in an arranged marriage with each other, all so that Ryunosuke's family tea shop will stay in the family.
• En Shinohara from Usotsuki Lily has such a strong dislike for men that he can't even look at his own reflection. It's for this same reason that he takes up crossdressing. Hilarity Ensues as the series is about he and his new girlfriend trying to work around the issues this causes.
• Souta from Wagnaria!! was this when he was little (he's the only son in the family and was raised like a girl), and then needed to do it again in ep 9 and 13.
• The tenants, particularly Yuki, frequently dress up as women for various convoluted reasons in The Wallflower.
• Wandering Son has Chizuru, a middle school girl who likes blurring rules and gender roles due to commonly wearing the boys uniform to school. She goes to an all-girls high school and it's unknown if she drops the habit. Chizuru strictly crossdresses at school as she's never shown wearing anything too androgynous outside of it.
• W Juliet has Makoto Narita, the male lead, who dresses as a woman because he made a deal with his father that if he spent the last two years of high school as a girl, he could pursue his dream of becoming an actor instead of inheriting his family's dojo. Also, his friend and later lover Ito Miura might count, but she's more of a Bifauxnen (she never tries to keep her gender a secret, and she occasionally complains about almost always being cast as a guy in the drama club's plays).
• In The World God Only Knows Yui Goudou started doing this after she returned to her body. She even admits guys' clothes are better.
  • And she gave Keima female uniform, while saying that it is something he needs for their future. Keep in mind that she is trying to conquer him. And later, he actually wears it!
• Yoshinori of Yubisaki Milk Tea is a high school boy who got drafted into wearing a wedding dress for a photo shoot and found that he liked cross-dressing, creating a female persona named Yuki. He ends up attracting admirers in both his male and female guises, but remains (mostly) straight, and he anguishes over the thought of giving up Yuki in order to mature.
• An enemy example occurs in one episode of YuYu Hakusho. Yusuke and company are storming the compound of a demon-exploiting tycoon and have to have off with his guards. One of them appears to be a girl named Miyuki (and honestly looks like such), so Kuwabara backs down while Yusuke holds no such qualms. During the fight, though, a quick grope up top and down below told Yusuke he didn't need to take it easy on him, so he didn't. The only dirty looks later were directed towards Yusuke for acting like a pervert.

Arts

• One of the male dwarves in Las Meninas is dressed in women's clothing to amuse the princess.

Comic Books

• Barracuda: Emilio, now Emilia, is a servant on the Spanish ship carrying Dona del Scuebo and Maria. He cultivates a troubled identity. Dressed as a young girl, he is sold as a slave to Mr. Flynn, who teaches him how to handle weapons and then becomes her lover. Emilia learns that he is being chased by a villain named Morkam. Morkam having killed Flynn, Emilio inherits from his mentor and decides to avenge him.
• Black Moon Chronicles: During Ghorgor Bey's time in a travelling circus, the ringmaster put him on the role of the diaphanous young lady in a Romeo and Juliet-type play (Ghorgor was then a strapping ten-foot tall half-ogre with Perma-Stubble). And yet the crowd loved it, even when the balcony collapsed under his weight.
• The DCU:
  • Danny the Street, in Grant Morrison's, (sensing a theme here?), Doom Patrol, is a transvestite sentient street.
  • Quality Comics's Madame Fatal, the first cross-dressing superhero. "She" was really Richard Stanton, a retired actor who took up the persona of a harmless-seeming old lady after his daughter was kidnapped. Because no-one suspects the old lady.
  • George (who is either a cross-dressing woman or a transgender man, the comic never elaborates) in Grant Morrison's Sebastian O is one of the more sympathetic characters in the comic. Not that the bar is particularly high.
  • Sir Ystin, the Shining Knight from Seven Soldiers (and yet another Morrison creation) is a girl disguised as a boy. The New 52 version seen in Demon Knights is a different matter...
  • Superman's Pal Jimmy Olsen has disguised himself as a woman... more than a few times, actually. He's rather good at it.
• The Disney Ducks Comic Universe has Donald Duck, who has absolutely no problem crossdressing if it's the practical solution to some issue.
• Empowered: And then there's the Goddamn Maidman! A burly, hulking, Batman style Badass Normal hero who also dresses up as a French maid. Complete with panties and fishnet stockings. Although there is a bit of humor wrung out of it (for example, the Hypocritical Humor of Maidman considering his own costuming choice normal and being an Animal-Themed Superbeing embarrassing, or when Maidman admits that part of the reason why he's The Dreaded is due to his providing in-universe Fan Disservice), for the most part, he's presented as a competent crimefighter and a genuine Nice Guy. There's also no hints of him being gay, trans, a Drag Queen or "perverted"; he just thinks a French maid outfit makes a neat costume for crime fighting.
• Fence: The comic has Bobbi who likes dressing up in girl's clothing including hair decorations.

Comic Strips

• 91:an Karlsson: Titular soldier 91 is typically depicted wearing his uniform. However, he has disguised himself in anything from a bridal gown to Easter Witch attire for practical reasons (which his superiors usually don't object to), and has also been shown wearing the traditionally female Lucia gown just for fun on the cover for the last 91:an number of 1983.

Fan Works

• Celadon's New Blossom:
  • The plot of the fic revolves around Ash becoming Erika's student. To go along with this, he must pretend to be a girl until he defeats the Pokémon League. Ash is initially embarrassed and annoyed by this, but he admits that he's rather cute as a girl and the clothes aren't too bad.
  • It's implied that James' interest in cross-dressing extends beyond just doing it for disguise purposes.
• In the final chapter of Gankona, Unnachgiebig, Unità, Italy cosplays as Sailor Moon. Let's just say it left very little to the imagination.
• Both Mitsuuru Takahashi and Shugo Kino in Pretty Cure Heavy Metal are this, with the only exception being when they're attending Isuten Junior High. Outside of school, Shugo takes the Real Women Never Wear Dresses trope to whole new levels, such as her swimsuit including short shorts and her Cure Hendrix costume including hot pants. Mitsuuru himself was forced to crossdress by his own parents, seeing that they were spending so much money on their firstborn Yuki alone, making it impractical, if not impossible, to buy new clothes for a second child, even if said second child was a boy. Despite being enrolled in MacArthur Grade School for the Arts as a boy, he had to wear his sister's old uniform. This continued for so long that by the time he was able to wear a boy's uniform for once when he attended Isuten Junior High, he was pretty much used to cross-dressing and by that point was willing.
• Harveste Addams of the Harveste Series by kyaru-chan, in which Harry Potter is raised by the Addams Family as a middle child named Harveste Addams. Harveste, who has a conveniently gender nonspecific name, passes as a woman mostly because she can hide more weapons in dresses than suits.
• At one point in the third chapter of The Melancholy of Haruki Suzumiya, Haruki has Mitsuru wear a maid outfit for a photo shoot.
• In the Hooker Verse, The Nostalgia Critic wears a corset and skirt. Of course, the 'wholesome' part is a little debatable given that he's, well, a hooker, but...
• In one Neon Genesis Evangelion fanfic, Shinji raids Asuka's clothes to try out cross-dressing in an effort to gain acceptance from his father who raised a girl instead of him. Of course, Asuka throws a fit when she finds out as she thinks Shinji and Kaworu (who happened to be on-scene) are doing perverted things (they aren't, the fic is entirely SFW); once she calms down, she offers to correct Shinji's appearance.
• Happens in Chapter 17 of A Day Indoors. Negi wonders if the frilly pink panties were necessary, really. Yuuna certainly seems to think they are.
• I Woke Up As a Dungeon, Now What? has Maryk (aka Olivia, aka Fiola, aka Naïlynn, etc), who despite not actually being trans (by Word of God), still uses predominantly female alternate identities.
• In Jade Green Eyes a salesperson in a store Harry visits is a man dressed as a woman, who suggests that Harry crossdress during the summer to avoid the fanatical attention of the post-Voldemort wizarding world.
• In the Many Quirks Persona series, both Akira and Yu enjoy crossdressing for various reasons. Akira takes it up as part of his job at Crossroads and takes to it too well, using it as disguises to spy on Akechi and mess with Ryuji, and even roping several of his fellow thieves into it. Yu treats it as Serious Business from the get-go, jumping at the chance to take part in the "Miss" Yasogami pageant, and even donning a voice changer to complete the image.
• DJ cross-dresses in Total Drama Do Over, as required by a challenge, taking the name DJette. He doesn't find it humiliating in the slightest.
• While it isn't touched upon that much, a Noodle Incident in Harry Potter and the Endless Night implies that Harry has no problem with wearing Integra's school uniform.
  Integra: His sense of style is rubbish. Do you remember the one time I let him dress as he wanted to?
  Ms. Pinkstone: But it was cute how you two matched.
  Integra: Please, he looks awful in all of my dresses and you know it.
  Harry: You said I looked great in your school uniform.
  Integra: Harry, skirts and dresses are two different things.
• Miraculous Ladybug fanfics Two in one and Day 11: Fashion (both stories written by the same author) depict Marc Anciel favoring wearing dresses during fashion shows, with practically no one having a problem with it.
• Harry Potter in Harry and the Shipgirls can pull this trope to the same level as Astolfo. To wit, when the Gryffindor Chasers got Harry caught up in a prank that forced him to wear female clothes for a week, he proceeded to milk it to the hilt, and left many of the male students at Hogwarts questioning their sexuality by the time he was freed from the jinx that caused this.
  • More recently, the Tsukumogami for the weapons of Astolfo himself have made their debut. Considering they're male and female versions of Rider Astolfo, it's extremely safe to say they are just as skilled at this trope.
• In The Disapperance Of Goro Akechi, Kanji's Phantom Thief outfit is a stylish black-and-gold gown. Rise boasts that Kanji was the winner of Yasogami High's Crossdressing Pagent two years in a row, with Kanji admitting it would have been three if Teddie didn't steal the crown during his first year.
• Team JNPR in War of Remnant: A RWBY Anthology wear opposite gender cloths for the dance in Volume 2. Jaune and Ren wear dresses, while Nora and Pyrrha wear suits. Ren even goes the extra mile to wear heels, saying he wanted to feel pretty.
• In ByAnyOtherName, Wei Wuxian dons his foster sister's clothes in order to pass as Wu Yingtai. It's a very effective disguise.

Film — Animated

• Cinderella III: A Twist in Time: Jaq and Gus dress as Lady Tremaine and the Fairy Godmother when telling Cinderella that Prince Charming forgetting her is not what she thinks, and he's under a spell causing him to forget her and marry Anastasia.
• The Lion King (1994): Timon ends up in a skirt in one scene ("What do you want me to do, dress in drag and do the hula?"), though since the animal characters don't normally wear anything it's debatable as to whether this counts.
  • In the P.O.V. Sequel, Timon was still wearing the outfit when he reunites with his Ma and Uncle Max, and they don't comment on it until after Timon has left the scene.
• Madagascar: Escape 2 Africa: Near the beginning of the film, when the four main characters are about to leave on the plane, Maurice appears with a cake that King Julien pops out of wearing a combination of cheerleader and hula outfit that consists of a coconut bra, grass skirt, and grass pom-poms. Of course whether this counts or not is unknown as he normally does not wear any clothes except for his crown. This also interestingly plays with certain Wild Mass Guessing, to whether if Julien is gay, bi or pan in addition to his gender identity, due to him being a male ruler when lemurs are matriarchal, leading to the audience to wonder if he is trans man or nonbinary, who allows his fellow Animal Gender-Bender subjects access to gender affirming care through a Back-Alley Doctor.
  "Which of you is attracted to me?"
• Mulan: The title character is disguised as a male in order to replace her sickly father during a war.
• Pinocchio and the Emperor of the Night: Scalawag and Igor use cross-dressing in an attempt to save Pinocchio from his illusion.
• Rango: The title character wears a dress in order to pass as a travelling actor to get some arrest-ees to let their guard down. It turns into an elaborate wagon chase scene, with him still in the dress.

Film — Live-Action

• All three protagonists of The Adventures of Priscilla, Queen of the Desert, to varying degrees. Terence Stamp plays a hard-drinking but patient trans woman, Guy Pearce a bitchy, high-strung Performance Artist, and Hugo Weaving is the timid, sweet-natured drag queen who persuades them to do a cabaret act in the middle of the desert. That breaking sound you heard was your brain.
• Colette: Missy, who habitually dresses as a man, is portrayed positively (many people then felt differently about this however). As Missy has an ambiguous gender identity though this might not be case.
• In Don Juan DeMarco, the title character (played by Johnny Depp) is at one point enslaved, and sold to a lusty Sultana. To prevent the Sultan from discovering her new personal attendant is an entirely 'unaltered' male, she disguises her new toy (most fetchingly!◊) in a loose-fitting jeweled sari. (One could suspect that the script-writers invented this to showcase Depp's talent for female impersonation, but it's actually lifted from Lord Byron's epic poem Don Juan.)
• Dragonslayer: Valerian turns out to be one. This was begun by her parents to spare her from the lottery of virgin girls being sacrificed.
• Played more than usually straight in Ed Wood: Ed is shown to be a heterosexual who happens to find women's clothing more attractive and comfortable. This is probably because he was based on an actual person.
• Forever Young: A major plot point involves four boys performing the Dance of the Little Swans for their performing arts college's festival in place of four girls when three of them die in a road accident and the sole survivor suffers a serious injury afterwards.
• Hussar Ballad: A young girl, Shura, dresses as a man just for a masked ball at first, but later uses that disguise to enter the army and serves as a real Hussar officer.
• In Just like a Woman (1992), the main character is a cross-dresser who was thrown out of his apartment when his fiancée found women's underwear inside and thought he was cheating; after starting a relationship with another woman more accepting of cross-dressing, he learns that his boss intends to defraud their Japanese clients, and he goes in disguise, dressed as a woman, along with his girlfriend, to foil the plot. This film was based on the 1985 novel Geraldine: For the Love of a Transvestite by said other woman, Monica Jay; Geraldine is the main character's en femme name in both the book and the film.
• In Kinky Boots main character Lola may be a performer who can dish out some truly mean words when she needs to, but when faced with ignorant and homophobic comments actively spreads understanding. 'Ask any woman what she likes most in a man: Compassion, Tenderness, Sensitivity. Traditionally female virtues. Perhaps what women truly want is a man that is fundamentally a woman.'
• Maurice and his fellow Drag Queens in Last Vegas initially come off as a joke about accidentally hitting on creepy crossdressers, but Sam quickly befriends them and Maurice later shows up at the party in normal business attire with his wife.
• Miracle Mile: The transvestite at the diner is treated as a normal person and free of Camp Gay stereotypical behavior, which is suprising in a film from 1988. She's an accepted regular at the diner and spends a good portion of her dialogue simply trying to give proper directions across town to a businessman. When Harry tells everyone about the harrowing phone call he just answered, the rest of the diners start to panic, but she calmly dismisses it as a Prank Call.
• Onmyōji (2001): Seimei lets down his hair and dresses up as the goddess Ame-no-Uzume in order to open the gate to the realm of the gods.
• In Pret-a-Porter (Ready to Wear), Danny Aiello plays Major Hamilton, a buyer of sensible clothing for the Montgomery Ward catalog who is secretly a high-fashion loving transvestite. As he spends his days during Paris' fashion weeks buying up product for his company to sell to middle America his wife Louise, played by Teri Garr, combs the boutiques of the Champs-Elysees, searching for lovely things in XL for him. Near the end of the film they spend a quiet dinner together, both in couture gowns and makeup and she tenderly compliments him on looking "beautiful, like Barbra Streisand".
• Several in Racing Daylight, which takes place half during The American Civil War and half in the modern world. Back in time, Rev. Potts (played by John Seidman) is married to Henrietta (actress Denny Dillon) who "we all knew was a man". In modern times, Seidman plays Busy-Body, who is either a cross-dressing gay man or a pre-op transgender woman. Dillon plays the Gossip, who wears overalls and fixes trucks and objects to being called a woman. Another male character paints his toenails in a whimsical moment, while a friend chortles "Nobody's telling RuPaul to take off HIS dress."
• Sappho: Sappho dresses as a man in Greece multiple times, and is presented positively overall. Characters who know about this disapprove or react with mixed feelings however.
• The '50s comedy film Some Like It Hot. Originally Joe and Jerry did it to escape The Mafia, but they kept up the act... and Jerry took his new role very seriously.
• Stardust: Captain Shakespeare is revealed to like dressing in women's clothing right at the same time he's shown as not really being a bloodthirsty murderer, but a good, kind man.
• Disney's Swiss Family Robinson had Roberta, who was disguised as a cabin boy by her father to protect her from the pirates.
• To Wong Foo, Thanks for Everything! Julie Newmar has John Leguizamo, Patrick Swayze, and Wesley Snipes all as cross-dressing drag queens. Vida and Noxeema even convince Chi-Chi to give up the boy she has a crush on to the girl in town who likes him, as it wouldn't be fair to him.
• Tootsie. While Dustin Hoffman's character starts out playing a woman simply in order to get work, he ends up playing the part in real-life as well.
• In Trainspotting, Begbie makes out with a "woman" in his car for a while before discovering it's a man.
• In both the film and the play of Victor/Victoria, the lead is a woman who crossdresses as a male, then gets a job as a female impersonator in a burlesque show. Also an example of Recursive Crossdressing.
• In Waiting for Guffman, director Corky St. Clair might be a closeted example. He often buys clothes for his wife Bonnie, a reclusive lady who nobody ever seems to have met.

( One of the girls in Miss Foster's show in Watch Your Stern is played by a sailor in a wig.

• Welcome to Marwen: Mark, who likes women's shoes (particularly high heels) and collects them. Nicol mentions her brother also likes women's shoes and clothing too. They aren't depicted badly as a result.
• One of the "edgy" things about Baz Luhrmann's modern remake of William Shakespeare's Romeo + Juliet is having Mercutio (played by Harold Perrineau) show up to the Capulets' ball — imagined in the remake as a Halloween party — dressed in drag. He stays in drag for a lot longer than is really necessary. Then again, it's Mercutio. He also dances and lip-syncs to "Young Hearts Run Free". It's awesome.

Literature

• Older Than Print: The medieval Arab and Turkish epics were replete with cross-dressing — both males as females and females as males. The legendary hero al-Battal crossdresses to sneak into the Greek emperor's palace, and his son Madhbahun disguises himself as a princess to lure the wily villain Uqba into his clutches. In Sirat Dhat al-Himma, the Muslim warrior queen dresses up as a priest and kisses the Greek princess Nura.
• The Afterward: Olsa likes to dress in both female and male clothing, not for disguise but just due to her whim it seems. No one who knows about this cares, though apparently other thieves believed she was "confused" because of it, and tied this into her being bisexual (which she denies).
• Out of all the characters in Anpanman, tough guy Kamameshidon is the character on the heroes side that is the most likely to crossdress. When he gets a starring episode with a female character, it's very likely that he'll end up crossdressing as her. Thanks to his rice bowl head and deep voice...he is not that good at pulling it off. His friends, Tendonman and Katsudonman, have also crossdressed, just not as often as Kamameshidon does. This possibly could all be based on a single pun, as "okama" is Japanese for a male crossdresser.
• Jacky in The Anubis Gates, living in 1810 London, is a Sweet Polly Oliver seeking to avenge the death of her fiance. In her society, she finds that she has much more freedom of movement and action by posing as male.
• In Aria the Scarlet Ammo, this is Kinji's brother's method to activate Hysteria Mode (which is triggered by sexual arousal). The result is so convincing that Aria thinks Kana is Kinji's ex-girlfriend. And it actually seems to create a Split Personality. You can't get more "wholesome" than that.
• Baka and Test: Summon the Beasts's Hideyoshi is one, naturally. But since he has an identical twin sister, the cast and us can let it slide. The fact that Hideyoshi's a boy, that is.
• In the Bloody Jack series, the eponymous Jacky Faber's adventure begins when she disguises herself as a boy in order to open up more opportunities to escape her dangerous life as a homeless orphan on the mean streets of nineteenth-century London. Her plan works. From then on throughout the series, she dons male garb whenever necessity or whimsy calls for it.
• One of the male regulars at Callahan's Crosstime Saloon is a professional Marilyn Monroe impersonator, and a very convincing one at that, to the point that he's often hit on while at work. He's also a happily heterosexual married man with a wife and kids.
• CLAMP:
  • Yuki Ajiadou from the light novel series CLAMP School Paranormal Investigators is a boy who dreams of becoming a famous actress. To that end, he wears the girls' school uniform.
• Discworld:
  • This is of course a core theme of Monstrous Regiment. Apart from Sweet Polly Oliver (or rather Polly Perks, who chooses Oliver as her nom de guerre because of the song), there is also passing mention of a male officer named Wrigglesworth who was known for playing cross-cast roles in his boys' school, and who is noncommittally described as being keen on "amateur dramatics" by the brass.
  • Nobby Nobbs also develops shades of this after disguising himself as the exotic dancer Beti in Jingo. He discovers he thoroughly enjoys hanging out with the other women of Al Khali, and on returning to Ankh-Morpork occasionally dresses in drag in the course of his duties.
• Epithet Erased: Prison of Plastic: Giovanni’s “Vincent Murder” outfit is not particularly feminine, but it does include a skirt. (A very evil skirt.) Despite being a self-proclaimed supervillain, Giovanni is a kind person who helps the protagonists.
• In the Evil Genius Trilogy Cadel crossdresses several times as a disguise, starting in his disguise class at the Axis Institute and continuing whenever he needs to escape some kind of surveillance. He has a whole alternate identity for his female persona - Ariel Schaarp.
• Louis from The Extra Man until he decides it's not for him.
• The Famous Five: George, from the otherwise hilariously backward children's series by Enid Blyton.
• Fate Series:
  • Fate/Zero: Saber dresses in a business suit and looks very good in it and continues to crossdress in the sequel.
  • Fate/Apocrypha: Astolfo. His looking like a lady (and even playing up gender ambiguity) has been joked about even in universe! This kinda leads into an Unsettling Gender-Reveal played for laughs when Jeanne ends up seeing Astolfo walk out of the shower stark naked. Bear in mind, at this point, she somehow (in spite of her True Name Discernment skill, which should have clued her in) didn't know Astolfo was a guy. Hilarity Ensues, with the end result being Jeanne letting out a very high-pitched scream and Astolfo laughing about it even on the following day, while Sieg expresses disbelief that Jeanne DIDN'T know.
• Franklin: In Franklin and Friends, Franklin has no problem dressing up as his favorite superhero, Dynaroo, despite Dynaroo being a female superhero.
• In The Goblin Emperor, there is Kiru, who presumably continues to wear more practical men's clothes after the attempt to deceive her potential employer about her sex failed and she got the job regardless.
• The Good Lord Bird: In the Live-Action Adaptation, Onion puts on a dress as a disguise early on, and gets mistaken for a girl after that by Brown, necessitating that he continue it. Finally he tries to confess what happened, but Brown stops him (apparently already knowing it) and says this doesn't matter, only the person Onion is.
• Haganai: As soon as Yukimura joins the group, Yozora insists he wear women's clothing at all times to "strengthen his inner manliness". This lasts until it's revealed, to the surprise of everyone (including him), that he actually is a woman...at which point Yozora starts making her dress in men's clothing. Yukimura has no problem with any of this.
• Xianming Lin of Hakata Tonkotsu Ramens is a cross-dressing assassin who is initially sent out to kill the main character, but ends up working for him instead. He initially cross-dresses as part of a disguise during operations, but eventually does so even outside work as he feels it helps him maintain a connection with his long-lost sister.
• In Hands Held in the Snow, Tia Knoll, the very rich and very sly nobleman, crossdresses in almost every appearance so far. Nobody comments on it much beyond curiosity, but he likes to flaunt his sparkly wigs and dresses.
• In Harry Potter and the Order of the Phoenix, Sirius mentions Fletcher has been dressing up as a witch as a disguise after Sturgis lost Moody's best invisibility cloak when he was arrested.
• Haruhi Suzumiya: Not one to let her middle class scholarship namesake have all the fun, Haruhi has her moment when she's allegedly Disguised in Drag in chapter 3 of Disappearance.
• Rin Mitani of Hensuki: Are You Willing to Fall in Love with a Pervert, as Long as She's a Cutie? dresses as a boy during the school day, but once it's done he wears the girls' uniform before heading to the student council. The rest of the student council is fine with it since it lets him perform his duties more efficiently and they became used to it anyway.
• Gasper in High School D×D wears the school's female uniform and pulls it off so well everyone needs to be told he's a he on first meeting. It doesn't help that he acts shy and feminine, to the point of quickly developing a crush on Issei. Issei tries to get him to start wearing more masculine clothing, at first because it creeps him out, and later because Gaspar's cross-dressing turns out to be rooted in trauma from his Dark and Troubled Past and he wants his friend to move past that.^note The crossdressing itself is treated as a harmless symptom by itself
• Ayumu from Is This A Zombie?, as he's drafted into a Magical Girl army after his zombie nature absorbs most of Haruna's powers, including the ability to transform into a Masou Shoujo.
• Yozak from Kyo Kara Maoh! is a 'spy' who, though taller and more muscular than his fellow bishounen, loves to disguise himself as a woman. A cheerfully flirtatious woman, even. He even carries a dress around, just in case he needs it.
• Jacob from novel Lagoon is simply fascinated by women's fashions, the cuts, the colors, the fabrics - he thinks men's clothes are simply boring. In Nigerian society, it is enough to make him suspect but he is shown as a decent guy.
• Last Night at the Telegraph Club: Tommy Andrews is a lesbian drag king whom Lily grows interested in after seeing her ad in the paper, visiting the club where she performs. She's revealed to be a nice, friendly woman. The police, however, view her as a terrible deviant seducing girls into being lesbians like her, which she's arrested for along with the club owner toward the end of the book.
• According to L: change the WorLd, L did this for an entire year at one point, as part of an investigation.
• Éowyn, so she can fight in the final battle, from The Lord of the Rings.
• In Loveless, Sunil, who's nonbinary and uses he/they pronouns, is fine with dressing in masculine or feminine clothes, and likes playing "gender-confused" roles in plays. He also requests to cosplay as Velma Dinkley for Georgia's surprise for Jason to try winning the latter back to Shakespeare Soc.
• In The Many Horrors Of Being A Tokyo Waitress most of the characters work as crossdressing waitresses at a gay bar. It is just a job, and they get used to it. Jonas, the main character goes home wearing the costume to save time.
• The lovely Ms. Fate lives in the Nightside, and is a genuine old-school superheroine who happens to be played by a man.
• Nezumi from No. 6 frequently has to dress as a woman in order to perform his act in plays, and makes a rather convincing woman at that.
• Nory Ryans Song: Patch wears a girl's long skirt, which is to protect him because of superstition dictating that the sidhe of Irish lore always look to steal away young boys.
• The main cast of Otoko no Ko wa Meido Fuku ga Osuki!? are four brothers who help their parents' Maid Cafe, and dress accordingly. The middle brothers usually crossdress only for work or other cafe-related business, while the oldest and youngest brothers crossdress all the time. In fact, the oldest brother, Nao, is so feminine that the girls at school pretty much treat him as one of their own and let him use female toilet and changing room without problem.
• Lee from Out of Position, who mostly crossdressed to fool football players like Dev and just because he wanted to. He stops after Isolation Play.
• Overlord (2012) has a pair of adorable dark elf twins, Aura Bella Fiora and Mare Bello Fiore. The former is a a girl who dresses and behaves as a guy while the latter is a guy dressing and behaving as a girl. A bit of a subversion on the "wholesome" part, since both are evil, but so are all the main characters in this series.
• In the Paradox Trilogy, Basil is the alien equivalent of a crossdresser, dyeing his feathers to have the brown coloration of an aeon female rather than the gaudy colors of an aeon male. Not being familiar with aeon biology, Devi doesn't realize there's anything unusual about his coloration until he explains.
• Plonqmas: Plonq's gay roommate Giblet dresses in a feminine slutty reindeer costume in “A Plonqmas Tale — 2019.” It's for a good cause, though — he's a self-described "Sexy Santa's Helper" at a Christmas party to benefit needy families.
  Giblet was dressed in what the snow leopard could only describe as a red-sequinned onesie with white faux fur lining the openings for the legs, armless sleeves, and a low cut V down the front. He complemented that with sheer fishnet stockings and black, knee-height, high-heeled boots. Across the back of the costume, split by the zipper were the words, Santa's "Helper" (Plonq chose not to wonder why the word "Helper" was in quotes). He completed the costume with thin, elbow-length black gloves, clip-on antlers, and plastic mistletoe tied tastefully above his tail with a piece of red ribbon.
• Raffles: in "The Rest Cure", Pretty Boy Bunny makes a fairly convincing woman when in drag.
• In Realm of the Elderlings The Fool, while his gender is never explicitly stated, switches from a female persona, Lady Amber, to a male persona, The Fool depending on the situation he is in and people he is with.
• Played With in River of Teeth. When she learns that the gang needs a white, moustached man to run an important errand — and their former candidate is not available — Archie promptly throws on a very convincing disguise of a white, moustached man. Everyone's astonished at how handily she had such a disguise available and thinks that she may be cross-dressing due to being a conwoman, but Archie reveals that she is actually gender-fluid and sometimes simply feels like a man and wants to be seen accordingly.
• Rose of the Prophet: Mathew easily comes off as an extremely beautiful woman while he dresses as one. Even prior to this he had been been mistaken for one. He is a good man who'd been forced to cross-dress, though In-Universe it's viewed as a capital offense after Mathew supposedly attempted seducing a man by wearing this (that wasn't what he'd intended).
• the secret lives of Princesses: Prince S switched places with his lookalike sister as a bet. Even as he got older, and his beard grew and he grew out of dresses, he braided his beard and had his dresses custom made.
• Slayers does this once a season, one episode per season (except seasons 4-5). Fans of the series refer to this as Episode 17, as each crossdressing episode is the seventeenth episode in the given season (and this came from the first season's alphabet-based Idiosyncratic Episode Naming—the seventeenth letter is Q, creating a "queer" implication). Ironically, not just the male cast, but often support characters introduced in the episode itself as well. Perhaps the most bizarre example is the "drag-on" sea dragon in the first season, who Gourry defeats by scratching its face and forcing the dandy dragon to retreat lest it gain any defacing scars.
• Song at Dawn 'Lady' Sanchez is a man pretending to be a lady. Dragonetz notes that the signs are there but no one would notice unless they were looking for them.
• A Song of Ice and Fire: Men who want to become Moonsingers must dress and live as women. In many cases, it's said outsiders cannot tell if the moonsinger is a man or woman at all due to this.
• Alanna from Song of the Lioness. During her time, girls were not allowed to be knights so she had to disguise herself as a male to receive training.
• Terence, the squire in Gerald Morris's The Squire's Tales, crossdresses to help rescue Sir Gawain from a dungeon.
• Sally Sweet in the Stephanie Plum series. He's described as not exactly attractive and nearly every other sentence out of his mouth is a Cluster F-Bomb, but he is depicted as a basically nice guy (even if he's the only school bus driver around who carries an Uzi under his seat).
• The Stormlight Archive: Ardents, the priestly caste of the Vorin religion, are allowed to ignore most of the usual Vorin rules for gender roles: Ardents can eat men's or women's food regardless of their gender, male ardents are allowed to be literate, etc.
• While Nanami's gender in Sukisho is never explicitly discussed, his clothing is mostly ambiguous regarding gender, and the non gender specific pronouns of Japanese are of no help either, everyone treats him like he always acts. His winter coat, pink bunny slippers, and the outfit he wears in the kitchen at home, places him firmly into crossdresser land.
• The Tillerman Family Series: A variant in the first book, Homecoming. Thirteen-year-old protagonist Dicey pretends to be a boy when on the run with her younger siblings, because she thinks she'll get hassled less as a boy. Since she has short hair and androgynous-looking clothing, she already gets mistaken for a boy pretty regularly so she just leans into it.
• Even after she's stopped performing in the music halls in drag, The Protagonist Nan of Tipping the Velvet is more comfortable in men's clothing and continues to wear her costumes.
• Natsume, from Tokyo Ravens dresses as a boy in public, as her family's tradition requires of the female heir.
• Shinobu Nanjou and Kouta Asada in Tsuki Tsuki! are forced to wear a maid and a Chinese dress at the sports festival. It's very convincing.◊
• Pulaski, the cross-dressing killing machine in Undead on Arrival, is one of the more heroic characters in the novel. When asked why, he says his older sisters dressed him up like that for fun, and he kind of liked it.
• In The Walker Papers series by C.E. Murphy, Joanne's friend Billy Holiday is a crossdresser who is also a respected police detective and happily married with children.
• The briefly-appearing "Lillie Longtree" in Welkin Weasels: Vampire Voles is an actor who usually plays female roles, and wears a red riding hood when out walking in the forest "to confuse the beasties". It should probably be noted that Maudlin asks about this "with a touch of envy in his voice".
• Whateley Universe:
  • Numerous characters, being Transgender, dress as the opposite gender until they have the opportunity to change physical sex. Others have already done so, but choose to wear the same clothes that they always have done. Phase is a wealthy boy who looks entirely female except for the genitalia, forcing him to have custom made clothes with a masculine cut but a feminine fit except for a loose groin. Presumably many other students in Poe house, though they are not mentioned.
  • Although there is one character who is not in Poe Cottage and cross-dresses. Gotterdammerung cross-dresses because he likes it and the story that focuses on him has him unsure if he should cross-dress for Halloween.
• The heroine of the Romance Novel Whisper To Me Of Love is revealed to be this when her disguise comes off while she's grappling with a would-be victim (she's a pickpocket). She admits to disguising herself as a boy to escape the advances of degenerates (but given the Crapsack World that the slums of London area depicted as, this probably wouldn't keep her much safer).
• In Karl May's Winnetou series:
  • Tante Droll (Aunt Droll) is famous as a "Westmann" who looks like a woman (fans are still divided between those who see him as just looking a bit feminine and those who see him as an outright transvestite).
  • Old Surehand's mother is an example of a tough lady disguising herself as a man.

Live-Action TV

• 30 Rock: Jack Donaghy reveals that he exclusively wore hand me downs until he was 12. His older siblings were all girls.^note "Apollo, Apollo": Season 3, Episode 16
• Accused: Simon, in his guise as Tracie. This even gets him acquitted, as he goes into court dressed as Tracie and successfully shows how ridiculous the idea of committing a crime in that outfit would be.
• Reality TV example: Derrick Barry on America's Got Talent and Courtney Act on American Idol.
• Mr. Humphries of Are You Being Served?. In one episode, he helped out by cross-dressing by pretending to be a female customer to help Mrs. Slocombe get her job back.
• Kate/Bob in Blackadder II and Goes Forth is a Sweet Polly Oliver, but admits she "actually prefer[s] wearing boys' clothes" (to the confusion of Lord Flashheart, who's always more comfy in a dress). She's also the most wholesome character in the entire series, bordering on Incorruptible Pure Pureness. Flashheart himself could count as an example, too. He’s not exactly wholesome, per se, but he is still manly despite his cross-dressing.
• Blankety Blank: Done as a career by Scouse comedian Paul O'Grady in his creation of the embittered, alcoholic, chain-smoking and sexually promiscuous Lily Savage, billed as "The Blonde Bombsite". Lily's savage and acid takes on life graced British comedy TV for quite a few years: she hosted the small-money gameshow for several years. Despite her literally savage persona, the fact that the person offscreen was male never mattered, let alone being implied to be any kind of problem.
• The original premise of 80s sitcom Bosom Buddies was Disguised in Drag, but the boys carry on with the charade over the course of the series longer than seems strictly necessary.
• Boy Meets World examples:
  • In S4E15 ("Chick Like Me"), Cory plans on dressing as a girl to school in order to find out how life is different for female students and male students. He turns out to have too masculine of a walk, so Shawn tries teaching him how to act female, getting it "surprisingly on the nose" according to Topanga. When he shows Cory how to walk like a woman and gets it perfectly, Cory and Topanga decide that Shawn should be the one to dress like a woman for the day. He turns out to be a babe. He also has a preferred "female" name (Veronica) and admits to having thought about doing this a lot before Cory ever decided to write the article.
  • In the much later episode "What a Drag", Eric Matthews decides that the only way for him and his best friend to avoid a local psycho and his gang, after almost getting them arrested, is to crossdress. They immediately turn to Shawn for help, and Shawn gives them a whole series of tips on how to crossdress correctly, so he clearly hasn't stopped since. Eric also decides to continue cross-dressing after the episode ends, just for his own sake. Notably, both characters are not only heterosexuals, but they are also actually three of the show's most prolific flirters.
• Cold Case: In "Best Friends" butch lesbian Billie likes to dress in a fancy men's suit whenever she can, to reactions varying from surprise to horror. She's a nice young woman (though she puts on a tough exterior, which is not too surprising given this) who's actually been arrested for this in the past.
• Comedy Central:
  • A frequent fixture in Lip Sync Battles, as both male and female performers will impersonate singers of the opposite gender. Perhaps most famously when Zendaya and Tom Holland competed against each other; Zendaya did "24 Karat Magic" by Bruno Mars, while Tom did "Umbrella" by Rihanna.
  • A Subverted Trope in the series Strip Mall, a male character is seduced by a supposed cross-dresser (but who is actually played by a very obviously female woman).
• Coronation Street, of all things, introduced Marc (aka, sometimes, "Marcia") in 2011, the show's first cross-dressing character (though Hayley, introduced in 1998, is a recurring Transgender character.) The show portrays Marc's dressing as both healthy and acceptable, with only unlikeable characters being against it.
• Simone, the likable twelve-year-old heroine of the Swedish children's programme Dårfinkar & Dönickar, based on the book by Ulf Stark, spends a while masquerading as a boy at school.
• Degrassi:
  • Degrassi: The Next Generation: Dave wore a long frilly skirt to prove a point when Adam made him uncomfortable.
• In the pilot of Drake & Josh, it's revealed that Josh dresses up as a woman in order to write an advice column for the school newspaper. Of the two brothers, Josh is easily the nicer and kinder one.
• The Dukes of Hazzard: The Season 6 episode "Targets: Lulu and Daisy" — where a diamond thief and his henchmen learn that Daisy and Lulu have accidentally gotten hold of a suitcase containing a stolen necklace — has, at Bo and Luke's behest, Rosco and Boss Hogg dress as Daisy and Lulu, respectively, hoping to lure the thieves into a trap. Plenty of bad jokes abound until the thieves kidnap (and plan to kill) the sheriff and the county administrator.
• EastEnders also introduced one in the form of Les Coker, who enjoys dragging up as "Christine". Deconstructed as it's treated as a Dark Secret by his wife Pam, and when it gets out, several residents (most notably Billy Mitchell) turn against him. A major part of their story arc was Pam learning to accept Christine, which she eventually did.
• Eat Bulaga!: The Lolas—played by Jose Manalo, Wally Bayola and Paolo Ballesteros (who made a career of himself doing drag performances and makeup transformations on Instagram and elsewhere)—in the "Kalyeserye" segement. Their antics were so much of a hit among audiences that some have watched the segment more for the comedy skits than the Al Dub pairing itself.
• Fellow Travelers: Frankie is a gay drag queen, while Real Life lesbian drag king Stormé DeLarverie is a minor character and friend of his. Both are nice, sympathetic people.
• Charlie Watkins, a CONTROL agent on Get Smart, is such an exceptional undercover agent that he looks exactly like the Real Life (and 100% female) actress Angelique Pettyjohn, and is known as Agent 38 on account of his impressive bust measurements. Charlie's all man, though, and evidently quite heterosexual, as demonstrated by his flirting with Agent 99.
• Golden Girls: Throughout the series, Dorothy's brother Phil's cross-dressing is Played for Laughs up until the episode with his funeral. Sophia reveals she was actually deeply ashamed of her son's cross-dressing, and while she claimed to blame his wife for stopping it, she truthfully blamed herself for it. Rose tells her that Phil was still a decent human being, and his cross-dressing wasn't anyone's fault, and that it's perfectly all right for Sophia to have loved Phil even though he wasn't "normal."
• Gossip Girl (2021): Max's dad Gideon is a kind man who also likes to crossdress sometimes. No one cares.
• Hill Street Blues: Jeffry Tambor played a cross-dressing lawyer who was doing so on advice from his psychiatrist to "resolve his feminine-identity issues." (The "cure" worked, and the same lawyer later became a highly-respected judge on the series).
• Subverted in Leave It to Beaver, where Wally is cast to play a saloon-girl in a "Summer Stock" Western; he hates the idea so much, that he ends up conning the perfect person for the role into taking it— Eddie Haskell.
• In season two of Legend of the Seeker, Zedd has to dress up as an old woman to infiltrate a castle. He seems to have a lot of fun with it, even when one of the (male) castle residents becomes infatuated with him.
  Richard: I think you have an admirer.
  Zedd: (affronted) Is there any reason why I shouldn't?
• Max Klinger on M*A*S*H was a wholesome, if definitely not attractive or believably female, crossdresser. In fact, the lack of believability was deliberate; he crossdressed in order to get a Section-8 "insanity" discharge from the Army. When Radar left, Klinger became clerk and dropped his cross-dressing gig, though this was written in due to the actor's discomfort with the idea that his now-mature children might be able to watch their dad cross-dressing on TV each week.
• In Monk, it turns out that Lieutenant Disher is good at being a female impersonator. In "Mr. Monk and the Missing Granny," he is seen disguised as a homeless woman, although Monk and Sharona see through it. Also, in "Mr. Monk and the Three Julies," he is disguised as their suspect's deceased mother's body as a trap to lure him out of hiding and get a confession. Their suspect falls for the disguise.
• Monty Python's Flying Circus:
  • All the Pythons have done this at one point, especially Terry Jones, who was very good at it. After all, dragging up is a rite of passage and an essential skill expected of any British male comedian. It's a rare big-name comic or comic actor who hasn't done this once in their career.
  • Also part of The Lumberjack Song lyrics, where the Lumberjack puts on women's clothing, hangs around in bars, wears high heels, suspendies, and a bra, wishing he was a girlie just like his dear papa. When the mounties recite the lines as chorus, they eventually get disgusted and leave.
• In the Canadian Disney Show My Babysitter's a Vampire Season 1 Episode 2, entitled "Three Cheers for Evil" the shows main characters Benny and Ethan must dress up as Cheerleaders 'Betty' and 'Veronica' in order to keep an eye on members of the squad they suspect are up to no good. They use the opportunity to try and get into the girls' locker room, are part of an all-girl sleepover and pillow fight, and are hit on by one of the supporting male characters while in disguise.
• Mystery Science Theater 3000: One episode had Mike Nelson take on the persona (and uniform, and wig...) of Captain Janeway to save the ship from falling into a black hole. He... kinda rocks it.
• Once in MythBusters, Tory wore a bra For Science!. Another time, while re-enacting a scene from Speed, he wore a wig. "Once again, making my parents proud."
• In Portlandia, Fred Armisen plays the feminine brunette Nina while Carrie Brownstein plays her boyfriend, the more masculine Lance (with a masked voice). They both do it convincingly.
• Jodie from Soap dresses as a woman a few times during his "I want to be a woman" phase in season one.
• This is a common occurrence in Super Sentai series:
  • In an episode of Dai Sentai Goggle Five that featured dolls coming to life, Miki/Goggle Pink disguises herself first as a male clown with a painted mask and just a slight change in voice, and later successfully pulls off a handsome prince disguise via a wig and a fitting outfit.
  • Then, in Choujin Sentai Jetman, the one cross-dressing was... Raita/Yellow Owl, in order to trick a Monster of the Week who absorbs women's voices. He successfully pulls it off, too - apparently, even fatties can make convincing women with just some makeup, a wig, and a kimono.
  • Soutarou Ushirogame/GaoBlack in Hyakujuu Sentai Gaoranger also pulled off cross-dressing as a bride. Even if he ended up striking the sumo pose and "Dosukoi!" yell.
  • Tetsu/DekaBreak in Tokusou Sentai Dekaranger seems inordinately fond of dressing up as a woman during undercover missions. Both times he's done it, he's caught the eye of a creepy buglike minor criminal stalker...who didn't care that it was a trap when Tetsu revealed his true gender.
    • In Magiranger vs. Dekaranger, he and Hikaru have to cross-dress again, much to the shock of Urara. Jasmine, however, is not surprised.
  • A more realistic approach is later revisited in Samurai Sentai Shinkenger, with Ryuunosuke/Shinken Blue. After all, he's a kabuki actor, thus cross-dressing is par on the course. It's even used in a plan, and it helps that the actor (Hiroki Aiba) is a Bishōnen by default. Ryuunosuke even said "he still has much to learn" after THAT much of a convincing act.
    • In the V-Cinema DVD Special had a bizarre moment where Kotoha and Mako dress and act like schoolboys... and then Ryuunosuke, Chiaki and Genta reveal that they're cross-dressers as well. Then Takeru, who's calmly sitting, suddenly flips his clothes and reveals himself to be a rather convincing cross dresser too.
• James Fitzjames on The Terror wistfully considers wearing a Renaissance-style costume gown to the expedition's morale-boosting carnival and admires the effect the dress has on him while holding it against his body, but ends up settling for the more plausibly deniable choice of dressing as Britannia, the patron goddess of the British Empire- still technically crossdressing, but less overtly because Britannia herself is depicted in masculine armor over her dress.
• Tipping the Velvet (2002): Nan finds that she's more comfortable in men's clothing even when offstage as this saves her from harassment by men, and thus starts dressing like that most of the time. She is always portrayed positively, never changing from a sweet young woman.
• One of the many subplots in one of the first-season episodes of Touch (2012) involved Norah and Shada, a pair of teenaged girls in Saudi Arabia who pose as boys just so that they can do things that women are forbidden to do, like drive.
• DEA Agent Denise Bryson on Twin Peaks, played by David Duchovny. (Who, as it turns out, has really nice legs.) She went undercover as a crossdresser for purposes of an operation, and found out she liked it better that way.
• Cissy Meldrum from You Rang, M'Lord?. She is a Bifauxnen, a lesbian, a crossdresser and a communist, but she is portrayed as one of the most positive characters in the series - a rare portrayal for the 90's. She gets on well with her family (except for her sister Poppy) and the servants, especially with the scheming butler Alf (who is a communist, too) and his daughter, Ivy the maid.

Manhua

• Ravages of Time: Xiao Meng, the eunuch assassin, insists he's a man but specializes in disguising himself as a woman.

Music

• The protagonist of the song "Cherry Lips" by Garbage.
• Desmond, the family man who "stays at home and does his pretty face" in "Ob-La-Di, Ob-La-Da" by The Beatles. Funnily enough, that lyric was a mistake made by Paul, but they left it in because they were sick of working on that song.
• "Bitty Boppy Betty" by Pink Martini is about a charismatic district attorney who dresses as a woman on the weekends, and who is the toast of her local nightclub:
  "You really can't ignore her,
  And if you don't adore her,
  There might be something wrong with you!"
• Vocaloid:
  • Kagamine Len is this in "Imitation Black" and other Visual Kei styled songs by natsuP. He is in "Servant of Evil," despite the title, he's a Love Martyr who crossdresses to pull a Twin Switch to keep his evil sister from being beheaded.
  • Kaito in "The Madness of the Duke of Venomania" does this to trick and kill Gakupo, who's been luring innocent women into his harem.
• The UTAU Ritsu Namine. His wholesomeness depends on how he's played, considering the fake breasts in his dress are working missiles.
• "Verbatim" by Mother Mother. The song describes a very effeminate man who nonetheless claims to be very heterosexual, and just enjoys the freedom it gives him.
  "I wear women's underwear,
  And then I go to strike a pose in my full length mirror,
  I cross my legs just like a queer
  But my libido is high when a lady is near."

Mythology & Religion

• Chinese Mythology: Lan Caihe of the Eight Immortals is depicted differently with regards to gender and gender presentation in different portrayals. It depends on who you ask.
• Classical Mythology:
  • According to some versions of the Minotaur's story, Theseus decides to switch two of the seven female victims with two very effeminate and brave boys disguised as girls. Said boys would have later freed the prisoners while Theseus was dealing with the Minotaur.
  • One of Hercules' punishments was to spend a year as a handmaiden to queen Omphale of Lydia, performing tasks like textile work, while wearing her clothes. Most art depicts Hercules in a dress gamely attempting to work out how this wool-spinning thing works, while Omphale lounges around wearing his lionskin and club.
• In the Tuvan epic poem Boktu-Kiris Bora-Seelei, the main character's sister takes on the appearance of her brother to bring him back to life after he is killed.
• Norse Mythology: In one story, Thor dons a full wedding gown in order to disguise himself as Freyja. It Makes Sense in Context.

Pro Wrestling

• " The Crush Girls 25th Anniversary Memorial Match" at NOSAWA Bom-Ba-Ye #5 Rongai One Night Stand saw Yoshihiro Takayama and Minoru Suzuki dressed as Lioness Asuka and Chigusa Nagayo against Kikutaro and Yoshihiro Sakai dressed as Dump Matsumoto and Bull Nakano.

Tabletop Games

• Exalted has a few cultural examples as part of the background:
  • In the West are the Tya, a "third gender" of women who adopt male social roles in order to work as sailors. This is mainly because the waters of the West are overseen by hag-like spirits known as storm mothers, who will try to sink any boat that's crewed by any woman prettier than themselves. Which is pretty much every mortal woman in Creation, and most of the dead ones. And a few horrible monsters.
  • The city of Chiaroscuro is overseen by the Delzahn, who are pretty firm on gender roles - men defend and supply the household, women run it but don't do much on the outside. However, it allows men and women the option of becoming Dereth - they basically can dress and act like the other gender, as long as they wear a gray sash at all times in order to avoid confusion.
• The Howling Banshees, an Eldar warrior Path in Warhammer 40,000 are traditionally an all female squad. Males, however, are permitted to join their ranks. Since the Banshee is a female spirit in Eldar mythology, he adopts a female persona and female armor when wearing his 'Warmask'.

Theatre

• Middleton and Dekker's 1610 comedy The Roaring Girl features one of these as a protagonist; unlike the cross-dressing heroines of Shakespeare's plays, though, she isn't disguised, and everyone in the play knows her real sex — she just likes dressing like a man. (The real person she is based on was slightly less wholesome.)
• Angel Dumott Schunard from RENT, who may also be Transgender. It's kinda hard with Trans Equals Gay thing that's there.
• Charley's Aunt: When the titular aunt fails to show up on time for a visit, Lord Fancourt Babberly dresses as an old lady in order to take her place and provide a chaperone for his friends' dates with their girlfriends, during which they plan to propose. Of course, things rapidly descend into chaos, but the good intentions were there.
• Shakespeare's Twelfth Night centres around Viola disguising herself as a man, and while it causes some issues in her love life, she is never presented as having done anything wrong.

Video Games

• AI: The Somnium Files has Mama, who similar to the Persona 5 example below is a friendly Drag Queen and the proprietor of a gay bar. She works as a Knowledge Broker for Date and flirts with him on occasion with his mild discomfort being Played for Laughs.
• In Akiba's Trip: Undead and Undressed, after a sidequest where the male main character goes Disguised in Drag, you can choose to have him wear girls' clothing from that point onward.
• Animal Crossing examples:
  • The first game and its GameCube re-releases allowed the player to wear any top they wanted, though they couldn't remove their hat/helmet, and boys wore shorts, green tights, blue sneakers, and tees while girls were relegated to dresses/dress-like shirts with blue and white tights, and red mary janes.
    • Animal Crossing: Wild World and Animal Crossing: City Folk allowed accessories and additional headwear to be worn or removed, with no gender-locking, and even provided opposite-sex hairstyles ^note though you still needed to have every hairstyle of the sex of your character, and you had to have you hair styled at least 15 times in order to unlock this in Wild Word and City Folk respectively, but this was still a bit limited.
    • Animal Crossing: New Leaf added skirts, pants, shorts, and dresses as separate kinds of items, instead of being permanently bound to your character forever if you chose to be male or female. Even it add three types of sleeves for tops and dresses. While it does specifically classify clothes as masculine, feminine, or unisex, it doesn't stop you from buying them or trying them on in the Able Sisters or GracieGrace stores, and the tailors will comment on it. Male characters will even do a Girly Run if they're wearing a skirt or dress.
    • Animal Crossing: New Horizons makes removes gender entirely in the English version, and clothes themselves are no longer designated by gender, as well. Now players don't have to have Mabel annoy them by asking if the skirt they're buying is a "present".
  • Simply named "Suspcious Cat" in Japanese hiragana, Blanca, the cat with the blank face, was internationally changed to female. The shirt she wore in the first three games could be mistaken for a dress, due to how long it is^note Bob, another cat, wears the same thing. Strangely, enough, her voice was initially that of female villagers in the GC ports, but was changed to a male one starting with Wild World in all regions.
  • Gracie the giraffe fashion designer, who wears fishnet-patterned, high-heeled boots, is a guy in the Japanese versions. Unlike with Blanca and Saharah, her male-to-female transition in International versions was due to her Okama characterization.
• It's hinted in The Binding of Isaac that all of the alternate characters in the game are possibly just Isaac wearing different wigs and accessories. This includes the three female characters, Eve, Magdalene, and Lilith.
• Bloodborne: You, the player, potentially. While most Attires are gender-neutral or look different depending on which gender equips them, the Doll Set and the Noble Dress noteably do not. So it's perfectly possible to be a man running around killing monsters in a Pimped-Out Dress or lacy doll clothes.
• In Catherine: Full Body, the character Rin is a kind male crossdresser who uses his powers to help the main character Vincent.
• Death Smiles II features Lei, who is a twelve-year-old boy wearing an Elegant Gothic Lolita maid outfit. Apparently, this is because this was the only outfit available to him when he arrived (and considering he was suffering from hypothermia, he didn't really have the luxury of being picky).
• Dragalia Lost has Chitose, Mitsuhide’s subordinate. He loves cute things, and his ultimate dream is to be the worlds cutest boy. That’s why Chitose likes to wear girls kimonos, and his 2D artwork even portrays him at a makeup station.
• Dragon Quest IV: Torneko is heavily implied to be one in remakes, as a way of hanging a lampshade on the fact that his ability to equip anything allows him to wear female-exclusive equipment.
• In Fallout 4, all clothing items have unisex designs, allowing cross-dressing of the player character.
• Fate/Grand Order:
  • Astolfo is a male who wears a dress. It amuses the others and he finds the outfit cute, so he doesn't mind wearing it.
  • Most of the Gender Flip characters are indicated to have passed for male during their lifetimes, due to politics precluding women in positions of power or in the military.
  • Saber Nero mentions that she sometimes dresses as a man for fun as well as for her job, but she never does so on-screen.
  • Le Chevalier d'Eon is portrayed as gender-neutral and androgynous in this game but is forced to disguise themself with a maid's dress on one of the story missions.
  • Another story mission requires you to infiltrate a party to locate a target, so your character goes disguised as someone of the opposite gender.
• Final Fantasy:
  • Faris from Final Fantasy V. One character even mocks her by saying, "We will fight like men! And women! And women who dress like men!" It doesn't help that she's probably the most masculine-acting of all of the player characters. The main character even mistakes her for a man.
  • In Final Fantasy VII, hero Cloud Strife has to rely on the help of some friendly transvestites so that he can disguise himself as a woman and infiltrate a gangster's mansion.
• Fire Emblem:
  • Forrest in Fire Emblem Fates crossdresses because of his love for female clothing, and because his father Leo once said he looked adorable in a dress when he was very young. He's so feminine that he's mistaken for a woman when his aunt Elise first meets him.
  • Rosado from Fire Emblem Engage dresses in a feminine manner because he likes cute and pretty things. He uses the female class outfits provided the class itself isn't male-exclusive, and while at the home base, he wears the female casual outfits as well.
• The first game of the Galaxy Angel II trilogy does this on Kazuya, but only if players choose to take the Natsume route. Kazuya ends up in a maid outfit as "Katherine".
• Ginyose Uzuki, one of the protagonists of Graze Counter. Apparently women's clothing is somehow required to properly handle Divider-type fighters.
• Bridget from the Guilty Gear series is a former example:
  • She was born as the younger of male twins, which was considered back luck in her village, meaning her parents would have had to either abandon her or put her to death. Taking a third option, her parents instead raised her as a girl. As she grew up, she ventured out to become a bounty hunter and prove herself as a man to dispell the superstition, so her parents wouldn't have to feel guilty anymore, but still continued to dress like a girl. Series creator Daisuke Ishiwatari admitted that the whole plot was just to make Bridget more interesting. As a result of continuing to dress and behave like a girl, Bridget was used for many Unsettling Gender-Reveal jokes, both in and out of the game.
  • One network illustration from Accent Core Plus shows Bridget wearing a girls' swimsuit on a beach with the rest of the Guilty Gear girls, despite not identifying as a girl at the time.
  • Bridget's arcade mode story -STRIVE- sheds this trope entirely. Having succeeded in proving her masculinity, she had tried living as a man, only for it to trigger her gender dysphoria, which causes her to leave home once again to figure herself out. After much introspection and confidence building, she comes out as a transgender woman. Daisuke has also revealed this was actually planned from the start, and there's Foreshadowing literally dating back to her bio released alongside the Japanese arcade release of 'Guilty Gear XX' as well as a number of hints dropped through things like official artwork (which would often group her with the girls) or interviews — where, in one notable case, Daisuke went out of his way to gender her female, only to "correct" himself in obvious annoyance, all the way back in 2007.
• In Ike Ike! Nekketsu Hockey Bu, the Nekketsu Hockey Team can wear the uniforms of defeated rivals. Among them are an all-girl school team who wear white blouses and red plaid skirts.
• Lamb from the indie game I'm Scared of Girls.
• The Legend of Zelda:
  • In The Legend of Zelda: Tri Force Heroes there are various costumes that grant Link special abilities if he wears them. These include Zelda's dress◊, a cheerleader outfit, and a Queen of Hearts dress.
  • The Legend of Zelda: Breath of the Wild has Link crossdress in order to enter Gerudo City to petition their chief for aid against Divine Beast Vah Naboris since voe (men) are forbidden from entering the city. Thankfully, the vai (women) who catch on to Link's true gender are either functional outcasts or Riju, all of whom have their own reasons for letting him stay despite this knowledge.
• Leisure Suit Larry:
  • In Leisure Suit Larry III, the main character is able to dress up in a silly show-girl outfit and thus turn on a female lawyer who likes to wear masculine underwear ("I had no idea you liked cross-dressing too!") like singlets and boxer shorts.
  • Also, in ''Leisure Suit Larry Goes Looking for Love (in Several Wrong Places)', you need to go to great lengths to dress up as a convincing girl (getting waxed, having your hair chemically altered to become long, blonde and curly, wearing a bikini swimsuit and padding out the breasts) to bypass some KGB operatives.
• Miitopia: The Pop Star class has two gendered variants, but it's purely aesthetic: the game has no qualms about you setting a male Mii in a female Pop Star's outfit and vice versa. There's also the Princess class with its fancy dresses that is completely open for males to take.
• The Magypsies in Mother 3, and, to a lesser extent, the girl they raised, Kumatora. Noticeably, the only Magypsy who doesn't crossdress is a traitor.
• Persona:
  • Persona 2 has Jun Kurosu, who not only has crossdressing listed as one of his official profile talents, but also has contact with Lisa demonstrating just how damn well he can cross-dress.
  • Persona 4:
    • Naoto Shirogane is a woman masquerading as a man.
    • Another example would be Teddie in his human form, who can pull off cosplaying Alice. The other boys in the cross-dressing pageant could count too, but the student body has rather negative opinions about it.
  • Persona 5 has Lala Escargot, a Drag Queen and the proprietor of a gay bar in Shinjuku. She is also one of the few people trusted by Intrepid Reporter (and Devil Confidant) Ichiko Ohya, and always has the Player Character's best interest at heart, cautioning him to be careful on his way home. The protagonist can work for her as a part-time bartender, and she's actually quite the benevolent employer.
• Pokémon:
  • In Pokémon Crystal, if you choose the female trainer, the overworld sprite changes from female to male if you do any game link cabling with any of the other six games. Yes, even with another Crystal version.
  • Everyone in Gym Leader Janine's gym in (Heart)Gold and (Soul)Silver is disguised as the Gym Leader to throw you off. Even the one guy, who gets defensive about it when the player fights him.
  • One of the Ferris Wheel date options for the male player character in Pokémon Black 2 and White 2 is a schoolteacher who, in the Japanese version only, takes off his shirt in the heat, and admits that he had to pass as a woman to get the job.
  • The Pokémon Kirlia and Gardevoir can both be male despite appearing to wear a tutu and a ballroom gown, respectively. Gen IV introduced Gardevoir's Distaff Counterpart, Gallade. Even in Gen IV and beyond, it's still perfectly possible to have a male Gardevoir, since Gallade uses a different evolution method. Wally's Gardevoir in Pokémon Ruby and Sapphire is male, though the remakes replace him with a Gallade.
  • Gothitelle looks as though it's wearing a dress with bows, but has a 25% chance of being male. Really, a lot of the more humanoid ones qualify.
  • Copycat from Kanto is a girl who loves mimicking others. According to official art, this includes dressing up as them (whether they're male or female).
  • Pokémon Café Remix gave out a Fancy Dress for Pikachu after releasing female Pikachu and Eevee. Male Pikachu can access the Fancy Dress.
  • In Pokémon Scarlet and Violet, most of the clothing options are completely gender-neutral. However, after completing The Indigo Disk, you can unlock Team Star's modified uniforms, which do come in specific male and female variations. You can wear either one regardless of whether you're playing as a boy or a girl.
• Nanashi, the protagonist of Shin Megami Tensei IV: Apocalypse, can put on some lolita dresses that can be bought in the Ginza members-only shop, and yes, they appear on his 3D model. It doesn't make him any less heroic.
• South Park: The Stick of Truth:
  • The game has Princess Kenny, who all the other kids present as "the fairest maiden in all the land", and who summons unicorns and wields heart-shaped arrows. She's also just a 10-year old boy in a LARPing dress and a bad wig. She holds up the "wholesome" by fighting at the New Kid's side until her Face–Heel Turn, when she becomes the Final Boss.
  • The New Kid can also end up crossdressing after a makeover from the Girls. There's a secret achievement for wearing the get-up while fighting Princess Kenny. Possibly subverted if the New Kid establishes themselves as female in the sequel.
• Mike in StarTropics crossdresses (or maybe magically changes gender) to enter an all-female village.
• Star Wars: The Old Republic: When the Sith Warrior visits the brothel where Vette's sister Tivva is enslaved, the madam, wearing a dancing girl outfit, asks them if they're looking for work. To Vette's amusement, the Warrior can reply, "I would look fantastic in your outfit," even if male. The madam replies they tried that before but it didn't work out.
• Story of Seasons: A Wonderful Life allows the player to pick either Shion or Maya's outfit from the start and purchase the other later, gender choice notwithstanding. Other outfits can be purchased from Van, again regardless of gender.
• From Suikoden V, Rahal dresses up as his sister to distract some guards. Those guards were not the only ones distracted; he looks exactly like his sister when wearing her dress and hairstyle.
• One of the outfit options for Mario in Super Mario Odyssey is a replica of Peach's wedding dress and veil, tailored to his measurements and complete with earrings and heels. Bowser thinks he looks amazing in it. Not that it matters since he wasn't invited to the wedding. As for Luigi, he doesn't think it's weird that his brother's wearing a dress, just that he's wearing a wedding dress for fun. Later, a dress based on Hariet the Broodal's was released, complete with stockings and heels. Again, Bowser thinks he looks amazing, while Luigi just thinks it looks familiar.
• Super Smash Bros. allows Miis to crossdress with some Mii Fighter outfits (such as dressing a male Mii as Viridi or Ashley, or a female Mii as Knuckles or Takamaru), but other outfits (such as the Inkling) automatically appear differently for each gender Mii.
• Tales Series:
  • In Tales of Vesperia, Karol can end up wearing a pink dress and a red hair ribbon for the sake of distracting a guard if you choose to. You can obtain this same costume for him to use all the time later on. Rita can also get in on this, as she has the costumes of Mao and Walter available for her to wear.
  • Milla from Tales of Xillia can wear the costumes of Stahn and Dhaos. She also has access to Asbel's costume in Tales of Xillia 2
• Daphnis in Tears to Tiara 2 crossdresses so he can follow Elissa everywhere as her bodyguard. He fools everyone at first sight and makes the goddess of war and barbarian princess complain about how to be ladylike.
• Tomodachi Life will let you dress Miis in clothes that don't match their gender. Miis don't seem to appreciate being put in opposite-gender clothing most of the time, so if you like making one or more of your Miis crossdress expect to hear the "doesn't like it" jingle again and again.
• Touken Ranbu, a game which features Anthropomorphic Personifications of Japanese swords as men, has Midare Toushirou, who fights while wearing a dress. It's this way because the weapon he's based on has a wavy line pattern and not a straight one. His powered-up Kiwame form ratchets up the girliness even further, with more frills and ribbons, giving the appearance of a Magical Girl.
• Twisted Wonderland: In Sam's New Year Sale 2023, Vil wears a female kimono, which is expected since he is Camp Straight. He's the first character shown crossdressing in the game.
• Utawarerumono: Dori and Gura, though this is only revealed in the game. Even then it is still confusing, as they are the only males shown in the whole series to have tails. At the very least they seem to like men...
• Any playable male character from The World Ends with You can become one if their Bravery stat is high enough. Bravery is used to determine what clothes characters can wear, with female clothing having a prohibitively high Bravery score that initially only Shiki can match, but any male character can grind their Bravery stat high enough to wear them as well. Subverted, in that the clothes don't appear on the characters' in-game sprites or portraits.
• Elihal in The Witcher 3: Wild Hunt is an elven Eccentric Fashion Designer who meets Geralt's friend Dandelion while dressed as a woman. He states that he's not gay, he just likes dressing up as different things and fantasized about being a doppler when he was little.

Visual Novels

• CLANNAD: In the After Story, Misae's friends had a bit of fun sneaking Shima-kun into their school wearing a girl uniform, ending up with someone that made them jealous for being so pretty while watching him turn the heads of every male they passed.
• Danganronpa: Trigger Happy Havoc: Chihiro Fujisaki. It becomes an important plot point in Chapter 2 due to where the murder occurred. During that chapter, it is also revealed that he resorted to pretending to be a girl in order avoid the constant pressure put on him for being a weak male, but this facade only resulted in him hating himself for not being able to face his own weakness.
• Fate/stay night: Saber aka King Arthur and in the Prequel she dresses in a business suit that looks very good on her.
• First Kiss at a Spooky Soiree: In NomnomNami's visual novel, there is a path where Marzipan bonds with the shy demon boy Baezel over their mutual love for video games, and Marzipan helps Baezel boost his confidence by having him cosplay as his favorite video game heroine.
• H₂O: Footprints in the Sand: Hamaji, who ends up marrying his best (female) friend, fathers a child, and still dresses like a girl.
• Hatoful Boyfriend: Ryouta Kawara tends to show up in girls' outfits at various points. It's played mostly for laughs since he's a pigeon. He's also the heroine's childhood friend and considering the good ending of the "Bad Boys Love" route, he's probably her canon love interest.
  • If you follow Ryouta's path in the full version, he has a job at a transvestite cafe so he can support his ailing mother.
  • Of course, for the school festival, the heroine's class decides to be a maid cafe, so everybirdie in class dresses up as maids— you only see the others in the full version, though.
  • In Holiday Star he proves to crossdress for many of his jobs, and Hiyoko notices he seems cooler and more confident dressed as a Magical Girl, but he sees no significance in it. Birds don't wear clothing much - to him, skirts are basically like an apron or any other uniform.
  • During a drama CD Ryouta and Sakuya encounter the upperclassman Yuuya in a maid outfit, waiting in disguise - and partly it might be to shock the easily shockable Sakuya, but Yuuya greatly enjoys wearing a dress. Official art of Yuuya in drag always has him much more gleeful about it than Ryouta.
• Highschool Romance: Shoji, the main character, is accidentally enrolled in an all-girl school, but the principal Lea decides to give him a chance at staying provided that he tries to pass as a girl, even buying him lingerie and clothes. Shoji himself, despite some initial embarassment, gets used to it, and during the course of the story he can befriend and romance two other girls. If Selene is chosen, it's revealed that Shoji took up crossdressing for his girlfriend's pleasure.
• Higurashi: When They Cry: Keiichi is forced to crossdress on at least two occasions as part of the club's punishment games. It happens even more frequently in the manga. The artist really seems to like throwing in fanservice of the various males of the series crossdressing, usually as mini-comics or splash pages between chapters.
• In Jack Jeanne, Jeanne casted actors would generally crossdress for their roles. The Rhodonite class students introduced (Except for Minorikawa and Ichinomae), however, played this more straight in contrast to the other Jeanne's, with the Rhodonite Jeanne's happily crossdressing and wearing typically girly clothes and enjoy fashion in general.
• Katawa Shoujo: Part of the reason Hisao thinks Hideaki is a girl upon first seeing him.
• Kira☆Kira: Shika is forced to crossdress against his will. Interestingly enough, despite getting more male fans than the real girls in the band, people do catch on that he's a guy through things such as the shape of his hands. He's quite relieved when he's allowed to stop not just because he was tired of getting hit on/thought of as a pervert because he was starting to get used to it. He's still a wholesome crossdresser five years later, in Curtain Call.
• Majikoi! Love Me Seriously!: Moro occasionally has had to suffer the indignity of crossdressing for some greater cause. Some members of the family would rather him do it more often.
• Mystic Messenger: 707 has a habit of cross-dressing and pretending to go by a different name. It's never plot-relevant, but he manages to confuse some of the other RFA members by being attractive in a dress.
• Nameless: Lance does this in his route in order to prevent Eri from acting in a play where she'd be kissed by Red. Sadly, it is never shown on screen.
• Otoboku - Maidens Are Falling For Me: Mizuho. He's so frightfully good at it, he makes all the girls gay for him. Or something. Hell even in one of the later episodes where one of the other characters is looking through her old picture album, we see him (as a little kid) in a girl's swimsuit.
• Steins;Gate: Ruka Urushibara has the personality of a polite, well-groomed and justified kind of beautiful girl. He doesn't push his opinions much upon others, but when he does he's quite bashful and blushes quite a bit. Because he's quite serious by nature, he simply believes what others say. He's a very shy person, and often turns down Mayuri's requests to cosplay. When they later manage to turn him into a real girl, the player as well as the main character are at first led to believe they failed, since she looks and acts exactly the same as before.
• Umineko: When They Cry: Sayo Yasuda, also known as Shannon, Kanon, and Beatrice is implied to be this in one direction or another. Of course, because Yasu's gender is never made explicit, no one's actually sure whether they're a girl cross-dressing as a guy or a guy cross-dressing as a girl. In the manga, however, it's implied that Sayo was a biologically male child who was Raised as the Opposite Gender.

Web Animation

• AoHaru Manga Library: In certain stories, the heroines are dressing up like guys for varying reasons. They don't even bother with changing names, except for Yui, who's usually changed to the more masculine 'Yuu'.
• Homestar Runner: As this page from the wiki demonstrates, every main character (and then some) has crossdressed at least once, with the sole exception of Bubs.
• Nijisanji: Aki Suzuya is a feminine boy who wears girls' clothing. His usual outfit includes a frilly blouse and skirt, and one alternate outfit is a Meido uniform.
• RWBY: Jaune Arc told Pyrrha that if she couldn't get a date to the school dance he'd wear a dress. At the dance, he realizes that she doesn't have a date because everyone thought she was out of their league and in a moment of vulnerability Pyrrha admits how isolated she feels. Jaune puts on the dress and asks her for a dance himself. He then keeps the dress on the entire night, completely comfortable in it. (For bonus points, Jaune's a Historical Gender Flip of Joan of Arc.)

Webcomics

• 8-Bit Theater: Red Mage, the delusional Munchkin, has a tendency to cross dress and pretend to be a woman named Deborah. He blames his father for this, but Thief states that he himself managed to put those memories into Red Mage's mind somehow. (Obviously, he stole them into it.)
• A-gnosis: In their webcomics, the Greek god Dionysos is portrayed as a Wholesome Crossdresser. For no particular reason; he just likes pretty clothes.
• Maxine/Max of Art School Sub Rosa is a female who's attending Art school as a male as part of a somewhat crooked "deal" to get a scholarship.
• Black Adventures: Black and N usually fight evil in skimpy Magical Girl costumes. Burgh and Elesa crossdress for fun (and to titillate the fans, apparently). The writer seems to have a thing for cross-dressing.
• But I'm a Cat Person: Bianca is a bisexual woman who cross-dresses.
• Castlevania RPG: Alec as stated by Cassandra Belmont.
  Cassandra Belmont: He makes a better-looking woman than I do.
• Charlie of Cirque Royale likes to wear skirts and dresses. His family sees no issue with this, with the exception that Claudette is annoyed that he takes her clothes. When he was younger he always dressed to match his twin sister down to the skirts, but has since grown out of it — though not the desire to wear skirts.
• College Roomies from Hell!!!: Paul "the transvestite stalker" - granted, a bisexual prostitute and a bit of a harasser, but still a generally positive influence on the cast once he becomes a genuine character rather than a Running Gag, serving as the voice of reason essentially whenever he plays a significant role.
• DOUBLE K: It appears that nearly 90% of Kamina's plans involve putting Simon in drag.
• Flaky Pastry: Leslie Audette, who is first introduced when Marelle and Nitrine are interviewing potential roommates. The author had originally planned for the two of them to be surprised by him (i.e. "Wait, you're a guy?), but then realized that Marelle wouldn't care, and Nitrine...would care either way.
• Footloose: Magical Transvestite Cherry, described on the cast page as "the only Magical Girl with a shred of humanity."
• Girl Genius: In the webcomic's "Cinderella" side-story, the three Jaegermonster men get cast as the ugly stepsisters. Maxim (in purple) really seems to enjoy the role.

  Oggie: (Hyu iz supposed to be an ogly stepsister. Whyfor hyu gots de pretty dress?)

  Maxim: (Hyu gots to know how to sveet-tok de costumers, dollink!)

• Girls with Slingshots: Darren
• El Goonish Shive: Parodied when avowed pervert (and frequent Gender Bender) Tedd is teased about trading school uniforms with Susan he vehemently protests that "I don't crossdress in women's clothing!" Susan muses that technically this is true. He crosses dresses in men's clothing quite frequently but never wears women's clothing while male (with two non-canon exceptions) and always changes out of any women's clothing he has on before reverting to male.
• Hetalia: Axis Powers:
  • Poland has dressed up in girls' clothes (usually miniskirts) in a few strips, which tends to weird out his Heterosexual Life Partner (or maybe not that heterosexual) Lithuania.
  • This is also part of Italy's backstory. Austria actually thought he was a girl until he hit puberty (it's somewhat implied that Hungary found out at some point, as she doesn't seem to be fazed by the discovery), and his first love Holy Roman Empire never found out that Italy was a male, always believing him to be a girl even when he left.
    • The child versions of Canada, Romano, and the US wore similar outfits. It's a Historical In-Joke.
  • As of Hetalia Bloodbath 2010, we've also had Hong Kong in a maid dress, and China in a qipao.
  • On the FtM side there was Hungary as a teenager, though she even managed to confuse herself with it, and so is maybe more an example of Raised as the Opposite Gender or possibly even being Transgender...or maybe an entirely different trope known as "Hungarian Gender Confusion" in the fandom.
• Homestuck: Jane is a sweet, caring, practical girl who also happens to really love wearing fake moustaches in the style of famous detectives from novels.
• Insecticomics: The Insecticons are fond of donning Barbie dresses and actually look quite good in them. It's hilarious. "Does this dress make me look fat, fat?"
  • Though they are Decepticons so maybe not quite so wholesome, then again they're usually too lazy to be evil and usually come off as Chaotic Neutral.
• Jet Dream:Dana and other Elle-Boys in the Remix Comic always dress as females but are fairly chaste and strictly heterosexual, apparently due to the (fictional) publisher's misguided attempt to pass The Comics Code and/or Publisher Appeal.
• Magical How: Fairies empower magical girls to fight evil. Only they seem to be a little confused about the "girl" part, resulting in a cast full of (ridiculously pretty) boys in skirts.
• Material Girl: The webcomic features a teenager forced into this.
• Ménage à 3: The very Camp Gay Dillon O'Brien, actually manifests this trope from time to time, as much of his cross-dressing is for purely theatrical purposes. At other times, though, it ... isn't. (Very little that Dillon does can be expected to be 100% wholesome.)
  • Sticky Dilly Buns: He continues to do so when he got his own comic, as he mostly dragged up for stage parts or as a practical disguise. When he talked the naive Ruby in that same comic into disguising herself as a man for one evening, that's certainly not sexual in her eyes.
• Moon Crest 24: This trope is played with when Derek dresses in Lucy's clothes after his first shower in months. Since Lucy threw out his old clothes in order to keep people from associating him to the Ice Titan's attack, she decided that it was a good idea to lend him her t-shirt and pants. Just until they go to Cool Topic to get him actual (emo) boy clothes.
• Queen of Wands: Felix occasionally crossdresses, and nobody makes a big deal about it.
• Rain:
  • Rudy is a gay male who sometimes crossdresses and calls himself Ruby. In contrast, Rain does not crossdress normally since as a transgender girl she identifies as female and dresses as such. However, when Rain is forced to wear typical boy clothes in order to not out herself to her brother, that is crossdressing (and the author knows that therefore this trope applies to her). Therefore, when Rudy poses as "Ryan's girlfriend" they are both crossdressing at that point.
  • And then there is Kylie, who chooses clothing to reflect the gender they currently identify as and never actually crossdresses if they can help it because it causes them to feel dysphoria.
• Skin Horse: Tip Wilkins is a cheerful ladies' man in a dress. He's fashion conscious and uses a variety of complex female outfits, but he makes no attempt to appear female (although given the art style, it can be a bit hard to tell). This is some kind of strange self-flagellation on part of the artist, whose previous Narbonic starred four obsessives who didn't always keep track of whether they were wearing pants.
  • Of course, it's also part of the Land of Oz motif, specifically to Princess Ozma.
• Spinnerette: Green Gable is the first male to inherit the costume. He hasn't bothered to change it in any way... such as by replacing the skirt with something a little manlier or getting rid of the pigtails. Maybe he believes Real Men Wear Pink, maybe he wants to stick to tradition, or maybe he's just not all that bright.

  The Werewolf of London, Ontario: (on GG going incognito as a nun) And what kind of disguise is that?! Try wearing pants, that would be a disguise for you!

• Supah Nario Bros: Toadsuke.
• SWAP Ensemble: Alfred Violon always wears a skirt or a dress. At one point, he dresses up as another male crossdresser, states that he's wearing boys' clothes for once, and tells people to stop making assumptions about his gender.
• TwoKinds: Natani, who literally has a male soul after her own was magically demolished. The conflict of male mind versus female instinct is an ongoing plotline, especially in regards to Natani's relationship with Keith.
• Umlaut House: In 1 and 2, there are a few occasions where Volair and Pierce dress in drag (like father like son). Plus that one time Rick switched his prosthetic body with a female one so he could pretend to be a woman for Jake's parents. Male cheerleading captain Jack Fusselton, on the other hand, wears a woman's outfit as a form of psychological warfare (and unlike the other examples is straight).
• Welcome to Room #305: There's Yoon Sung, who likes to dress up as a woman at night. Subverted when it's revealed that it's actually his twin sister.

Web Original

• Empires SMP: Exaggerated in Season 2. At Gem and Katherine's Princess Tea Party, every attendee is required to show up in a dress, or be kicked out and shamed across the server, regardless of their gender. Not only does every male server-member show up (which would be 8/13 of the season's main cast), but all of them are neutral, if not outright enthusiastic about showing up in a pretty dress, and a couple of them have canonically worn dresses of their own volition prior to the event.
• Paradise: In the setting, humans are randomly, permanently transformed into Funny Animals (and occasionally gender-changed) by causes unknown. A Weirdness Censor renders these changes Invisible to Normals, who continue to see the Changed as their original human selves (and genders). Any gender-Changed invariably ends up a Wholesome Crossdresser, since he or she cannot dress as the gender he or she really is or it will look strange to those not in the know. Affects some changes more than others, of course, as far fewer people will find anything odd in a "woman" wearing jeans than in a "man" wearing a dress.
• Randy Rainbow often dresses as and plays female characters, always for laughs.

Websites

• Channel Awesome: Quite a few of the staff members of the website has crossdressed in the various web videos that they have released with some examples listed below.
  • Spoony as Spoonette and The Gate Cleaner's Wife, Linkara as 80s Chick, Benzaie as Veronique and The Nostalgia Critic as an Airline Hostess.
  • Critic does this fairly often and has done since he was at least thirteen, expressing much embarrassment at the home videos of a teenage him in full drag. He was also Raised as the Opposite Gender for a bit, giving him a few issues. A nice moment in The Monster Squad review has Tamara wanting her cross-dressing as a boy acknowledged, and he dismisses it because he's cross-dressed for fun so much that it's not a big deal.
  • JewWario has actually cross-dressed in public on several occasions (most notably at showings of The Rocky Horror Picture Show).
  • Benzaie has made cross-dressing a running joke on his show for sketches about his more girly interests.
  • Tacoma from Demo Reel played Oprah for a parody and dressed as Belle from Beauty and the Beast to make Rebecca happy. He didn't mind either costume.
  • Malcolm Ray decides to be one of the members of Catwomen in Catwoman episode and you can clearly see that he's loving every moment of it. Maybe a little too much...
• Literotica: Par for the course in any story on the website that's in the Transsexuals/Crossdressers section and doesn't contain either magic or bondage.
• Tumblr: Possibly the most adorable example ever, The Prince and the Princess is about a young prince named Edmund who wants to be a princess.
• YouTube: Tamaki Inuyama is a male Virtual YouTuber who dresses like a girl. Fittingly, he's designed and voiced by Norio Tsukudani, creator of the Otokonoko manga Himegoto.

Web Videos

• Hey Ash, Whatcha Playin'?: While Ashly Burch is pretty far from "wholesome", she does rock some mean costumes of male characters in many early episodes.
• ZeroLenny: If there's a dress in the game he's playing, Lenny will put it on, and then proceed to beat the whole thing with a broken sword.
  Robolenny: (wearing the Antiquated Set) I'm a Pretty Princess.

Western Animation

• Several episodes of 6teen have Jude cross-dressing for various reasons, such as trying to get in touch with his feminine side, a disguise so he can get more doughnuts by donating more blood than is healthy, and trying to get into a dance where only single girls can get in. This is even highlighted in one episode:
  Jonesy: Why are you always the girl?
  Jude: It's my delicate bone structure.
• All Grown Up! has Phil dressed as his twin sister Lil. He seems to develop a crush on another boy.
• The Amazing Chan and the Chan Clan character Stanley Chan has crossdressed on more than one occasion, twice for disguises and one for the sake of being hilarious. He pulls it off quite well, too.
• In The Amazing World of Gumball episode "The Lady," it's revealed that Richard, unable to make any guy friends, regularly disguises himself as a woman named Samantha so he can hang out with a group of sassy older ladies. At first, Gumball and Darwin are not amused, as they believe Richard is cheating on their mother with Samantha, but once they realize the truth, they immediately try to stop Richard from breaking off his friendship with the ladies. Turns out two of the other ladies are actually men too.
  • "The Dress" features none of Gumball's clothes being clean, so he has to go to school wearing the only clean thing that's left: his mother's wedding dress. This ends up working well with him, as everyone treats him nicer. Unfortunately, Darwin (who's unable to recognize Gumball when he's wearing the dress) falls in love with him.
• Roger Smith from American Dad!. He himself is anything but wholesome, but his frequent cross-dressing is never portrayed negatively.
  • For around half of the episode "Beyond The Alcove Or: How I Learned To Stop Worrying And Love Klaus", Jeff Fischer is dressed in a French maid outfit and high heels.
• Gene from Bob's Burgers. Only so far has actually done this once, when the Belcher kids ran a casino out of the titular restaurant's basement, but he makes references to this every so often.
  • The transvestite hookers from "Sheesh! Cab, Bob?", despite their occupation, are another example of this trope. They're some of the most consistently kind and cheerful characters around. How wholesome are they? One of them is even voiced by Jack McBrayer (best known for playing Kenneth Parcell), playing very much to type.
• Examples from The Fairly OddParents!:
  • One episode has Chester dressing up as a girl so he can get a skating partner.
  • On the opposite side Trixie was a very convincing boy in The Boy Who Would Be Queen.
  • In part 3 of Wishology, Timmy's dad has been known to wear a dress with a blonde wig. However, this was All Just a Dream in the Darkness' Lotus-Eater Machine.
  • In the episode "Scary Godparents", Timmy's parents go out as each other for Halloween.
• Stewie Griffin in Family Guy has taken to this lately. While the most prominent example is Season 5's "Boys Do Cry", in which he dresses as a girl to escape a witch-hunting mob and ends up entering a beauty pageant during the Griffins' stay in Texas, he also dressed up in another episode and pretended to be Brian's girlfriend to spark jealousy on another girl. Men at the restaurant recognized his female persona, so he's obviously used it at least once before.
• Both Fred and Barney of The Flintstones do this oddly often. Barney does it VERY often in the Fruity Pebbles ads, presumably just to get Fred's Pebbles.
  • Barney also disguises himself as Fred's girlfriend in The Jetsons Meet the Flintstones so they can gain access to a poker game with Mr. Slate without being recognized.
• In season 2 of Infinity Train, Jesse and Alan Dracula (or at least the guy in his mouth) put on dresses for a fashion show themed car. It's probably the one of the few Western shows along with Steven Universe that doesn't present this as embarrassing or odd. The only part that can be considered funny is that Jesse has to wear the dress over his regular clothes.
• On Jimmy Two-Shoes, both Jimmy and Lucius do this while being flight attendants.
  • Jimmy ends up cross-dressing frequently during the series, whether it's for disguise purposes, losing a bet or because he felt like it.
• Carl from Johnny Bravo has dressed as a woman many times throughout the series course.
• Kaeloo: Stumpy is frequently Dragged into Drag, but once admitted, under the effects of Truth Serum, that he does enjoy dressing up as a girl. In Season 2, he frequently argues with Pretty about who gets to be the "girl", to her annoyance. This has led to some... awkward instances◊.
• Lilo & Stitch: The Series:
  • Pleakley continues the tradition of mostly wearing female Earth disguises, which is justified as having three legs leaves pants out of an option for him. However, while it is true that he wears them as a disguise, it is also true that he enjoys it such as the time he reenacted an old black and white airplane version of a Train-Station Goodbye with him as the woman and Jumba as the man or when he helped David try to get Nani jealous by dressing as a flamenco dancer.
  • Jumba cross-dressed once in a bridal gown so that Pleakley could get out of an Arranged Marriage. Sadly, the wedding itself was called off with arrival of Gantu, who scared off the wedding chapel owner just as he was about to finish the ceremony, leaving the pair currently unmarried.
• In The Little Rascals episode "Fright Night", Darla dresses so as to resemble Alfalfa.
• Looney Tunes: Bugs Bunny changes his gender presentation regularly. Most notably done in What's Opera, Doc?
• The Magic School Bus Rides Again: All four of the Friz girls do this for a segment set in the past, when time zones are conceptualized.
• The Penguins of Madagascar: In a continuation of the film examples (see film examples above), Julien wears a traditional Hawaiian hula skirt, and even drags Maurice and Mort into wearing the same thing.
• Rocko's Modern Life: Heffer's stepbrother Peter seems to like wearing the female version of an outfit if given a choice such as wearing cheerleader outfit complete with a skirt and a ballet outfit with a tutu instead of pants and tights respectively, which upsets his dad but not his mom.
• Scooby-Doo: Scooby and Shaggy occasionally do this, usually during the chase sequences when they're trying to hide from the monsters; either they pose as a couple on a date, skirts just make a quicker disguise, or they (usually Scooby) pretend to be a she-monster to lure out the presumably-male Monster of the Week (which always works, even though the monster is usually a human in a costume).
• SheZow: The titular character is a Legacy Hero superheroine whose powers and costume are granted to whoever wears her ring. Originally meant for women in the family line, the ring is worn by Guy Hamdon, a pre-teenage boy who inadvertently got stuck with it. As a result, he wears SheZow's female-intended costume as he fights crime. Guy doesn't take it well at first but quickly becomes indifferent to it.
• Several minor examples from The Simpsons:
  • Bart once demonstrated how to walk in high heels to help Lisa prepare for a beauty pageant. He was surprisingly good at it.
  • Later that season, in "Marge in Chains", he proposes breaking Marge out of prison with a scheme involving him dressing as a woman to seduce the warden and get the cell keys.
  • Homer and Flanders both lost a bet over a children's miniature golf tournament, forcing each to mow the other's lawn while wearing their wives' best Sunday dress. (Flanders, in what is probably a moment of Early-Installment Weirdness, comments cheerfully that it reminds him of his college fraternity days.)
  • In "Homer Loves Flanders", Homer fantasizes about looking at himself in a mirror wearing a wig shaped like Marge's hair.
  Homer: Heh, I don't need her at all anymore!
  • In "The Springfield Connection", Homer mentions that he occasionally wears women's underwear; something that he and Marge apparently agreed was "strictly a comfort thing''.
  • Once, puppies tore up all of Bart's socks, forcing him to wear a frilly pink pair of Lisa's. He also wears pink culottes because "I gotta coordinate."
  • In "Whacking Day," Abe reveals that, while he didn't actually ride out World War II posing as a German cabaret singer, he did wear a dress for a while in the forties. ("Oh, they had designers then!")
• SpongeBob SquarePants crossdresses surprisingly often, and seems to enjoy it quite a bit. Whenever SpongeBob and Patrick need to pretend to be a male and female couple, SpongeBob will almost always be the female (although it’s partly because Patrick doesn’t wear a shirt).
• Marco Diaz from Star vs. the Forces of Evil crossdressed to infiltrate St. Olga's Reform School For Wayward Princesses. He not only leads a rebellion but his Princess Turdina persona becomes an Icon of Rebellion and he receives monthly royalty checks for merchandise. When Miss Heinous exposed him to the other princesses (right when he was about to confess the truth himself, ironically enough), the princesses are accepting of the revelation, saying he can be a princess if he wants to. Even Marco's own parents don't bat an eye when he puts on his Turdina facade in front of them. It’s gotten to the point that one of the show’s most common fan theories is that Marco is actually a closeted Transgender woman.
• Steven Universe:
  • In "Sadie's Song", Steven Quartz Universe happily dresses up in a crop top, skirt, and makeup when serving as a last-minute substitute for Sadie Miller's musical performance. He's completely comfortable with this, and it's portrayed as the correct thing to do. Nobody judges him for it or even reacts to his attire, and it's not played for laughs or creep factor at all - the only comical part of this situation is that the audience had already guessed the "mystery act" would be Steven before the substitution was actually made.
    • In "Diamond Days", Steven has the Pebbles make a version of Pink Diamond's outfit in his size for him to wear at the ball because he feels he should "dress for the occasion". He doesn't seem to mind wearing it. The only factor that ever makes this uncomfortable for anybody is the fact that he's being shoehorned into his mother's old role on Homeworld during this arc.
• Tiny Toon Adventures: Buster Bunny, same as Bugs, often to trick people.
• Jerry from Tom and Jerry also cross-dressed a few times to trick Tom, who apparently is less likely to be violent towards a girl mouse.
• Toopy and Binoo do this in many of their episodes such as wearing princess gowns and high heels to go to a ball. The show brushes it off as normal and is quite progressive about it for a show that came out in 2005.
• Toot & Puddle: In Charming Opal, Puddle dresses up as the tooth fairy, hoping he can sneak into Opal's room and leave a quarter for her in exchange for her tooth. He ends up being too late because he and Toot fall asleep and by the time they wake up, it's morning. Turns out it doesn't matter, though; the tooth fairy came anyway.
• Unusually for a children's show (especially a Disney one), The Weekenders twice implies that Carver is a crossdresser when his friends catch him in possession of girls' clothing.
• Woody Woodpecker: The title character has done this time to time, the most memorable instances being Chew-Chew Baby, Drooler's Delight and The Woody Woodpecker Polka.

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