"Uh... Olsen, when we said that this story would call for staking out Luthor in 'casual dress'..."
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.
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 have any type of 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 "true" gender 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 crossdressing disguises more often than seems strictly necessary, this trope may apply.) Wholesome Crossdressers tend to enjoy dressing, even if only reluctantly, secretly, or subconsciously.
Generally does not overlap with Drag Queen (which is more about "performance" and theatricality) or Transsexual (usually a much deeper and more complicated subject), though there are exceptions.
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.
Kousaka from the Genshiken crossdresses to help the club sell doujinshi at a comic festival. His club mates find it disturbingly convincing.
Genshiken Nidaime introduces Hato Kenjirou, who crossdresses as a way of life, and never visits the club as a boy.
Huo Long from Haou Airen. His heart is in the right place, but he is a Triad member.
The very girly Aoi Futaba from You're Under Arrest! (who dresses as such after some self-discovery involving extensive undercover work) is virtually indistinguishable from the other female characters; post- Art Evolution his only barely male noticeable trait is being taller than other policewomen.
Aoi is more of a Transsexual then a simple crossdresser though.
A running joke in Koko Wa Greenwood (aka This Is Greenwood) is Shun being mistaken for a girl. His younger little brother is likewise androgynous enough to be distracting.
Hibiki-sensei in I My Me! Strawberry Eggs, who crossdresses 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.
Chou Ryuuen aka Nuriko in Fushigi Yuugi. 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 WholesomeCrossdressers (he and Nuriko were the only men convincingly looking like women, to the chagrin of the others).
Ouran High School Host Club 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 sexes.
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 crossdressing' is an insult to the profession.
Mizuho in Otome wa Boku ni Koishiteru. He's so frightfully good at it, he makes all the girls gay for him. Or something. Even the animators seem to forget his gender occasionally, judging by the swimsuit scene.
Mizuho is wearing a fake chest, although it is very convincing.
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.
Ciel from Black Butler. In episode 4 of the anime, he sneaks into a ball in a very...special outfit◊. Keep in mind that he's a a twelve-year-old boy who runs his own company. This outfit is infamous in the series, to the point of where it even has it's 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.
Jun from Happiness! makes such a realistically pretty girl he even has several male students in his fanclub (he used to be the main picture and its that convincing). Jun's only feature of maleness is the cast reminding us of it. The only obvious feature changed when he became a girl briefly is a larger chest, and he still had to mention it to his classmates.
In the Re:Lucks sequel/fandisc to the original Visual Novel, he's effectively the Gay Optionalthough it must be noted that one of the choices on his route is whether to 'have him' as a guy or (via magic) as a girl.
Dori and Gura from Utawarerumono, 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...
Tsubasa Kurenai from Ranma ˝, who's in love with Ukyo Kuonji, a Bifauxnen female crossdresser. A later character, Konatsu, also falls into Ukyo's orbit. It should be noted that Konatsu appears as a traditional Japanese kunoichi or female ninja.
Of course, Konatsu was raised 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 Ukyo 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 Ukyo 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 Ukyo for a real boy. Then they thought that "she" was a lesbian after they learned he had known Ukyo was really a girl all along (which greatly startled Ukyo herself, who had evidently figured that Tsubasa was a crossdressing homosexual guy who had been fooled by her disguise).
Later in the manga, Ranma, Ryoga, 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 crossdressing 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.
In the Mai-Otome manga, Princess Mashiro is replaced by her twin brother. The gags of the manga constantly poke fun at "Manshiro's" plight.
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.
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.
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 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 Luca first meets Hayate when he is cross dressed(long story). When she later sees him in his butler uniform, she asks if he's a girl who likes to wear boys cloths. How well Hayate fits here is even a bit of a Running Gag in the manga.
Fruits Basket features several wholesome crossdressers. Among the males of the Sohma family: Ritsu always wears women's clothing out of insecurity, Momiji dresses as a girl just because he likes it (he stops as he grows up), and Ayame is an equal-opportunity sort who runs a fetish costume shop.
Subverted in the case of Akito: shortly after we learn they are a Villainous Crossdresser, they turn into the wholesome variety (eventually they stop and accept themselves as their original gender).
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.
There's quite a few of these in Family Compo — the main character's adoptive family (his aunt and uncle) turn out to be gender-swapped — that is, the extremely masculine uncle is biologically a woman, the extremely feminine aunt is biologically male. Their daughter switched genders every few months as she was growing up, until deciding to stay female when she entered college — but the main character's not sure what she is biologically, which leads to most of the tension between them. The main character's also effeminate to the point that he ends up as the female lead in a student film, with a lesbian chasing him around, with a yakuza boss trying to convince him to get the "big snip"!
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.
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.
Yuki Nomura from the manga No Bra is a sweet, kind, beautiful and roommate Masato Kataoka's perfect girl. Except she's a he.
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.
Loran Cehack's female alter-ego Laura Rolla in ∀ Gundam.
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!".
Alto Saotome from Macross Frontier used to be a Kabuki actor 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.
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.
Subverted in one chapter of JoJo's Bizarre Adventure. The main character of Part 2, 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 Annasui from Part 6 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 Villainous Crossdresser, depending on who you ask.
Interestingly enough, he was originally intended by Araki to be female upon his introduction, only later being retconned to a male crossdresser. Over time, his appearance becomes much less feminine as well, with him pretty much being fully masculinized by the end of Stone Ocean (other than the women's clothes, of course).
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. 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.
Yozak from Kyou Kara Maou, though taller and more muscular than his fellow bishounen, loves to disguise himself as a woman. A cheerfully flirtatious woman, even.
In CLANNAD ~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.
Tokyo Godfathers' Hana is a woman who insists that "God made a mistake" by putting her in the body of a man. In fact, a former professional drag queen, and probably the best groomed of the homeless bums who are our heroes - also the first to take the Trash Bin Baby to heart. Has an extremely Girly Run and a bass voice.
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.
The Kamabakka Kingdom is, quite literally, "full of transvestites". Even the animals are into it.
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".
Izo, commander of the 16th division of the Whitebeard Pirates is probably the best example, as is maybe the only crossdresser who can't be spotted as one at first sight.
While they may be portrayed as nice people, they're also pictured to be rather unattractive. There are also quite a few jokes about them squicking out Sanji, so YMMV on the wholesome part.
Sanji◊ was humiliated and tricked into becoming a crossdresser himself. Fortunately, he got better.
In the original Sailor Moon manga, Naoko Takeuchi admits to drawing Haruka AKA Sailor Uranus manly when posing as a man. At the same time, the original Starlights are just crossdressers and don't ever change gender. None of this stops either Haruka OR Seiya from forming crushes on Usagi, though. Usagi herself does this in the anime episode "Cruise Blues" when she sneaks onto a cruise ship disguised as a handsome young freelance journalist. Also, the difference between Manga Uranus and Anime Uranus should be noted. In the anime, Haruka is drawn exclusively in men's clothes, and is mistaken as such a few times. Manga Haruka is shown wearing women's clothes just as often, even wearing the female School Uniform once she transfers to Juuban Highschool.
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).
Keiichi in Higurashi no Naku Koro ni 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.
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.
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.
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 a borderline Transsexual...or maybe an entirely different trope known as "Hungarian Gender Confusion" in the fandom.
While Nanami's gender in Sukisho is never explicitly discussed, his clothing is mostly ambigious 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.
Seiji of Midori no Hibi 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.
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.
From the fillers, there's Princess Toki of the Land of Birds, who is also impersonating her dead brother Sagi.
Butterflies Flowers: Domoto's coworker and very close friend Suou, of whom Choko is quite jealous until she realizes he's a he.
Used as a one-off gag in Game X Rush, where the middle-class Memori is portrayed as a "Cinderella" as oposed 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 escae, of course.
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).
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.
Miyashita Masashi from Onii-chan to Issho (official English title: 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 constantlycrossdresses 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 chagrine. Later, he admits that Sakura enjoys it when he dresses femininely, so it might not be such a bad thing after all.
Ash from Pokémon 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 this trope a couple more times, once as a Meido.
Souta from WORKING!! 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.
Nononono is a ski-jumping manga by the author of Elfen Lied. The heroine Nonomiya is crossdressing 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.
Kotobuki Seishiro (Seiko!) from Lovely Complex is very nice and friendly (a little TOO friendly with Ootani) who insists "god made a mistake" and put her into a boy's body. After The Reveal and fending off a few hateful comments, Ootani, Risa, and friends take him/her in as part of their group. Aside from some friendly teasing (often by wayofHaruka), Seiko seems to fit in and find a happy school life with little difficulty.
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!
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.
Lt. General Grumman disguises himself as an old woman at one point to meet with Mustang.
Wandering Son has this as a large part of its plot, as a feminine boy, Shuichi, and a tomboyish girl, Yoshino, begin frequently dressing in girl's and boy's clothing respectively, much preferring and wishing to be the other gender. They also befriend a transsexual named Yuki, who acts as a Cool Big Sis to them.
More accurate examples, gender-wise, would be Chizuru and Makoto. Makoto makes a cute girl when he dresses up, even though he thinks he looks bad due to his freckles and glasses (which isn't a bad thing). Chizuru is a girl who sometimes crossdresses as a boy, and she looks like androgynous.
The tenants, particularly Yuki, frequently dress up as women for various convoluted reasons in The Wallflower.
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. 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.
Kazuki in Get Backers. The writers, especially in the anime, will take any excuse they can to get him into womens' 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 womens' 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.
Eyeshield21 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 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.
Neon Genesis Evangelion's main character Shinji Ikari has crossdressed on two occasions, once wearing Asuka's spare plugsuit (complete with breast plates) and again when he and Asuka are training to defeat Israfel they wear identical ... "jazzercise" outfits.
Yozak from Kyo Kara Maoh is a 'spy' who crossdresses on a regular basis, to the point where he now carries a dress around just to have one handy. Which is quite hilarious, seeing as he's ripped and rather manly.
Cruz, from NEEDLESS, unwillingly cross dresses as a girl in the later part of the manga (and ended up popular with his team mates as well as the readers) in order to infiltrate an all-girls Academy. Later he gets a bounty on his head and had to remain cross dressing as a girl to avoid attention from his enemies. Its not known whether he will ever revert back to male clothing as his team mates protest against it when he mentions about it, thus he is STILL in girl's clothing. A popular nickname for this version of him is "Yamada-ko"
As of manga chapter 113, Cruz is officially changed into female by Blade's godly powers, to the amusement of the majority of his companions.
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.
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.
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.
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.
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).
Not one to let her middle class scholarship namesake have all the fun, Haruhi Suzumiya has her moment when she's allegedly Disguised in Drag in chapter 3 of Disappearance.
In Oh! Edo Rocket the reason for Genzo's crossdressing 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?
Nezumi from No6 frequently has to dress as a woman in order to perform his act in plays, and makes a rather convincing woman at that.
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.
The titular character from Kunisaki Izumo No Jijou, who is already attractive enough to be mistaken as a girl all the time, frequently crossdresses 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.
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.
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.
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.
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.
Ayumu Mikoshiba from Otasuke Miko Miko-chan is one, however reluctantly. A character introduced later, though, has no such qualms about cross-dressing.
In Hidan no Aria, 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 − at least according to Kinji, Kana and his brother are "different personnas". You can't get more "wholesome" than that.
Hime, from Himegoto, is forced to dress as a girl during school. In the spinoff Himegoto+, everyone in the main cast cross-dresses.
Quality Comics's Madame Fatal, the first cross-dressing superhero. "She" was really Richard Stanton, retired actor, who took up the 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 crossdressing 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.
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 crossdressing and by that point was willing.
It's revealed in Pretty Cure All Stars 3D: Live and Loaded! How About That! that he looked so convincing as a girl (despite everyone knowing he's a boy) that he got a girl's role in every play his class held, including Sakura Kinomoto from Cardcaptor Sakura (referred to as "Cardcaptors" in the fic), a play mentioned in episode 29 of PCHM. This streak continued into his junior high years, and his most memorable performance was as Suzumiya Haruhi (in that play, Shugo portrayed Kyon).
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.
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 crossdressing 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'm supposed to be the Grand Duchess Anastasia, but I think I look more like the Chrysler Building."
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.
One of the "edgy" things about Baz Luhrmann's modern remake of Romeo and Juliet is having Mercutio (played by HaroldPerrineau) 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.
And he also dances and lip-syncs to "Young Hearts Run Free". It's awesome.
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 make up and she tenderly compliments him for looking, "beautiful, like Barbra Streisand".
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.
Saga in Mitt liv som hund (My Life as a Dog).
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.)
The title character of Rango 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.
Disney's Swiss Family Robinson had Roberta, who was disguised as a cabin boy by her father to protect her from the pirates.
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.'
George, from the otherwise hilariously backward children's series The Famous Five by Enid Blyton.
The lovely Ms. Fate lives in the Nightside, and is a genuine old-school heroine who happens to be played by a man.
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".
Older Than Print: The medieval Arab and Turkish epics were replete with crossdressing — 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.
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.
Terence, the squire in Gerald Morris's The Squire's Tales, crossdresses to help rescue Sir Gawain from a dungeon.
Alanna from Song of the Lioness. During her time, girls were not allowed to be knights so she had disguise as one to receive training.
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).
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.
Yuki Ajiadou from CLAMP's 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.
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.
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.
One of the male regulars at Callahans 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.
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 crossdressing after the episode ends, just for his own sake. Notably, both characters are not only heterosexuals, they are actually three of the show's most prolific flirters.
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 memebers 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.
Max Klinger on Mash was a wholesome, if definitely not attractive or believably female, crossdresser. 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. However, having worn women's clothing for so long he found that his body had gotten used to the feel and he developed a rash unless he wore female underwear under his uniform. There was a kind of 'don't ask-don't' tell policy about it.
On 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).
DEA Agent "Denise" Bryson on Twin Peaks, played by David Duchovny. (Who, as it turns out, has really nice legs.) Also a rare case of a heterosexual crossdresser on network TV.
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.
Also subverted in Comedy Central's series Strip Mall, a male character is seduced by a supposed cross-dresser (but who is actually played by a very obviously female woman).
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.
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.
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 a BBC modern-dress production of The Taming of the Shrew, Petruchio was a rare Western media example of a heterosexual crossdresser.
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.
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.
Then, the V-Cinema DVD Special took this to ridiculously funny levels, when in a bizarre (long story) moment, Kotoha and Mako dress and act like school boys... and then Ryuunosuke, Chiaki and Genta reveal that they're cross-dressers as well. The biggest WTF moment was when Takeru, who's calmly sitting... suddenly flips his clothes and reveal himself to be a rather CONVINCING cross dresser too. What. The. Hell.
Simone, the likeable twelve-year-old heroine of the Swedish children's programme Dĺrfinkar & Dönickar, based on the book by Ulf Stark, spends a while masquerading as a boy at school.
Jack Donaghy of 30 Rock 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
British soap Hollyoaks features Kris, a bisexual cross-dressing man.
Dave in Degrassi wore a long frilly skirt to prove a point when Adam made him uncomfortable.
Coronation Street, of all things, introduced Marc (aka, sometimes, "Marcia") in 2011, the show's first crossdressing character (though Hayley, introduced in 1998, is a recurring Transsexual character.) The show portrays Marc's dressing as both healthy and acceptable, with only unlikeable characters being against it.
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.
Wallander offers us Louise, Kalle Svedberg's girlfriend.
Jodie from Soap dresses as a woman a few times during his "I want to be a woman" phase in season one.
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.
One of the many subplots in one of the first-season episodes of Touch 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.
Xiao Meng the eunuch assassin from Chinese manhuaRavages Of Time insists he's a man, but specializes in disguising himself as a woman.
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.
Pretty much everyone in Queen, in the video for "I Want to Break Free". Nice legs, Roger Taylor.
"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!"
"Who put the drag in drag queen? Don't knock it until you've tried it"
Kagamine Len is this in "Imitation Black" and other Visual Kei styled songs by natsuP. He arguably 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.
According to some versions of the Minotaur's story, Theseus decides to switch two of the seven female victims with two very effeminate but brave boys disguised as girls. Said boys would have later freed the prisoners while Theseus was dealing with the Minotaur.
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.
"The woman shall not wear that which pertaineth unto a man, neither shall a man put on a woman's garment: for all that do so are abomination unto the Lord thy God."
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.
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 Banshee's, an Eldar class in Warhammer 40K are traditionally an all female squad. Males however are permitted to join their ranks. But since the Banshee is a female spirit in Eldar mythology, he adopts a female persona and female armor when wearing his 'Warmask'.
Of course, sometimes a girl would try to get into acting by pretending to be a male actor. It is likely that they were considered feminine enough to play the roles of women. Including Rosalind.
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.)
Fancourt forced to chaperone as the titular Charlie's Aunt.
Bridget from Guilty Gear. The original story was that Bridget is part of a set of identical twins, which in his village were considered bad luck, and was sent to be a nun (either that, or he'd be abandoned to his death as a newborn), therefore his whole story path is him going Determinator and wanting to prove he wasn't a bad omen on anybody. His creator admits that making him a boy was, in the spirit of other characters in the game, to simply make him more interesting.
Despite his mannerisms and the promo artfeaturing him in feminine poses, Bridget does not actually identify as female. As far as he's concerned, he's just a boy in a habit who carries around a teddy bear and a yo-yo and really wishes people would stop thinking he's a girl.
Another example would be Human Teddie, who can pull off cosplaying Alice. Yu and Yosuke in the crossdressing pageant could count too, but the student body has rather negative opinions about it.
And on the topic of Persona, Persona2 has Jun Kurosu, who not only has cross dressing listed as one of his official profile talents, but also has a demon contact with Lisa dedicated to just how damn well he can cross dress.
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.
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.
It's not so much mocking as it is a playful jab. There's even a scene before you find out that the dude's a chick when Bartz and Galuf both go to check up on Faris to see if "he's" okay. They go into "his" room while "he's" sleeping. They both have a similar reaction: "Huh?" *speech bubble with a thumping heart* *look like they're laughing*). Interpret that how you will. And yet they continue to be surprised when the big reveal comes.
It was probably a Stupid Sexy Flanders moment, from how they got surprised of the revelation. They still called her a guy after that scene, anyway.
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.
Also, everyone in Gym Leader Janine's gym in (Heart)Gold and (Soul)Silver is disguised as the Gym Leader to throw you off.
The Pokémon Kirlia and Gardevoir can both be male despite appearing to wear a tutu and a ballroom gown, respectively. Gen IV introduced Gardevior's Distaff Counterpart, Gallade. Even in Gen IV and beyond, it's still perfectly possible to have a male Gardevior, since Gallade uses a different evolution method*
a Dawn Stone instead of leveling up
Similarly, Lopunny is based on a Playboy Bunny, but is just as likely to be male as female. 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.
You can wear any clothing or accessory items, even those that are obviously intended for the opposite sex. This extends in subsequent games to even unlocking the ability to have girl's hairstyles or shoes on a boy or vice versa. The only thing you can't do is change the face style or actually use the opposite sex clothes model (that is, putting a dress on a boy character will make it still look like a shirt, and putting a shirt on a girl will still look like a dress)- though, this last restriction is removed in the 3DS version, which has skirts, pants, and dresses as separate kinds of items. 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 store- the Able sisters comment on it but are okay with it. Male characters will even do a Girly Run if they're wearing a skirt or dress.
Blanca, the cat with the blank face, is evidently a male, even though "Blanca" is the feminine form, the gibber-clip is the highest-pitched one used for females, and the outfit is the female skirt. She has no name in Japan, and internationally she's been changed into a girl. Bob, another cat, is still a boy though purple and he wears a long pink floral "shirt".
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.
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).
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.
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.
Ryouta Kawara tends to show up in girls' outfits at various points in Hatoful Boyfriend. 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.
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.
In Kira-Kira, Shika is forced to cross dress 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.
Olivie from the Angelique series of dating sims for girls. Yes, he is a possible love interest in every game he appears in.
Sayo Yasuda, also known as Shannon, Kanon and Beatrice from Umineko: When They Cry 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 crossdressing as a guy or a guy crossdressing as a girl. In the manga, however, it's implied that Sayo was a biologically male child who was Raised as the Opposite Gender.
Tip Wilkins from Skin Horse is a cheerful The Casanova 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.
Paul "the transvestite stalker" from College Roomies from Hell!!!!!! - 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.
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.
Parodied in El Goonish Shive when avowed pervert (and frequent Gender Bender) Tedd is teased about trading school uniforms with Susan he vehemently protests that "I do not crossdress in women's clothing!" Susan muses that technically this is true.
TwoKinds has 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 with Natani's relationship with Keith.
In Umlaut House 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).
Red Mage, the delusional Munchkin of 8-Bit Theater 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.
Green Gable from Spinnerette 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!
In 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.
In 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.
In Queen of Wands, Felix occasionally crossdresses, and nobody makes a big deal about it.
Maxim: (Hyu gots to know how to sveet-tok de costumers, dollink!)
The very Camp Gay Dillon O'Brien, when introduced in Ménage ŕ 3, 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.) Later, when he got his own comic, Sticky Dilly Buns, the pattern continued, 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.
In webnovel/manga Cherry Girls, everyone (probably except Yuki) is this. Nao takes it further, with the girls even treat him essentially as female and even let him change clothes in girl's dressing room without any problem, and some of them really likes him for that.
Leslie Audette of Flaky Pastry, 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.
In the Paradise 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.
Numerous characters of the Whateley Universe, being transsexuals, 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.
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.
Timon of The Lion King ends up in a skirt in one scene ("What, you want me to dress in drag and do the hula?"), though since the animal characters don't normally wear anything it's debateable as to whether this counts.
Part of Override's bio from her toy on Transformers Cybertron (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.
In the episode "Scary Godparents", Timmy's parents go out as each other for Halloween.
Stewie in Family Guy has taken to this lately. While the most prominent example is Seaon 5's "Boys Do Cry", in which he dresses as a girl to enter 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.
She Zow is a Legacy Hero superheroine whose powers-enhanced costume are granted to whoever wears her ring. Originally meant for females in the family line, the latest member in the family line who wears the ring is Guy Hamdon, a pre-teenage boy. As a result, he wears SheZow's female-intended costume as he fights crime. Guy seems to be completely indifferent to this, although he didn't take it too well at first.
Carl from Johnny Bravo has dressed as a woman many times throughout the series course.
Director Ed Wood. A heterosexual transvestite (and apparently a bit of a womanizer in his younger days), he's probably one of the more famous real life examples of this trope.
Arguably, the entire Glam Rock movement qualified.
Eddie Izzard is this, and often mentions in his comedy shows that he is an "executive/action" transvestite, not a weirdo transvestite. He has also referred to himself as "a lesbian in a man's body" or "a male tomboy."
Many Visual Kei bands, especially kote kei, oshare kei, and lolita bands, have at least one crossdresser, often (though not always) the (lead) guitarist.
Quite a few of the talents under Japanese talent agency Johnny's Jimusho cross dress often, and well enough that it has lead to quite a few amusing fan sexuality confusion moments over time.
Tegoshi◊Yuya◊ IS Johnny's representative for this trope.
Danny Bonaduce was seduced by a cross-dresser, and found out only too late— just as the cross-dresser likewise found out too late that Danny was a psychotic ex-child star and martial-arts/steroid freak. Bonaduce spent time in jail, and the cross-dresser spent time in the hospital.
Pete Burns, the English singer-songwriter, has an androgynous style.
Julian Eltinge was famous as a female impersonator in the early 20th Century.
According to one unreliable source in a sensationalist biography, J. Edgar Hoover crossdressed while participating in homosexual orgies. Skeptics of the claim say that even if he had such proclivities, it's highly unlikely that Hoover would be so reckless and indiscreet about them, which would run counter to his general personality.
Most modern Western women now wear clothes and fashions that were first popular for men to wear long before (or were unisex). This is not really a chauvinistic boast—all sorts of things were once worn by men, such as skirts, pantyhose, stockings, high-heeled footwear, earrings, eyeshadow, perfume, etc. Some specifically form-fitting items (like brassieres) were always for women for obvious reasons. But in general, concepts of what define gender-specific or gender-neutral clothes are cultural issues that evolve over time.
This is actually a Double Standard, given that Crossdressing women seems to be looked down upon far less than a crosdressing male. A crossdressing woman might get comments of Butch Lesbian thrown at her, but a crossdressing man is likely to be seen as a Creepy Crossdresser.
Justin Bieberrevealed "I’ve worn women’s jeans before because they fit me. It’s not a trend; it’s just, whatever works, works." This is more common than you might think, because most men's jean sizes start around 28", and the legs tend to be cut larger. If a man's waist size is smaller (say 26") and/or he has thin legs, women's jeans would fit better.
Lady Gaga. No, not just wearing pants, she actually goes full Drag King with her alter ego Jo Calderone.
The Men in Tutus stage production, emphasizing the ballet maneuvers that full grown men are put through over the titular tutus and tights they're put in. Yes, including the Played for Laughs moves.
Similarly, and predating Men In Tutus by some years, the Ballets Trockadero de Monte Carlo.
Both the male-dressing-as-female and female-dressing-as-male varieties are common in the cosplay scene. The aforementioned Double Standard in regards to crossdressing is somewhat more toned down, and in fact, some conventions have fan-hosted panels on how to crossplay effectively.
The Hogettes are a group of male Washington Redskins fans who dress up like elderly ladies at games (and also have plastic pig snouts over their faces). They're named after "the Hogs", the offensive line of the Redskins during the late 1980's and early 1990's who could dominate the line of scrimmage and pave the way for big runs (in other words, they "hogged the road").
Vladimir Malakhov once donned a red wig and black tutu to perform a parody of Sylvie Guillem's performance of Gsovsky's "Grand Pas Classique". The real Sylvie Guillem was impressed.