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[[quoteright:217:[[JimmyOlsen http://static.tvtropes.org/pmwiki/pub/images/miss_jimmy_olsen_1512.jpg]]]]
[[caption-width-right:217:"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 [[CampGay 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.
-->-- ''Film/EdWood''

{{Crossdress|er}}ing characters who are presented in a positive (or at least neutral) way. Frequently presented as {{attractive|BentGender}} (or at least not ''un''attractive), 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 [[HaveIMentionedIAmHeterosexualToday 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 {{u|nsettlingGenderReveal}}sually resolved after TheReveal.

The opposite of CreepyCrossdresser. May overlap with DisguisedInDrag or its DistaffCounterpart, SweetPollyOliver. (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 DragQueen (which is more about "performance" and theatricality) or {{Transsexual}} (usually a much deeper and more complicated subject), though there are exceptions.

----
!!Examples:

[[foldercontrol]]

[[folder:Anime and Manga]]
* ''Anime/AstroBoy'' 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.
* 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 ''Manga/HaouAiren''. His heart is in the right place, but he ''is'' a Triad member.
* The very girly Aoi Futaba from ''YoureUnderArrest'' (who dresses as such after some self-discovery involving extensive undercover work) is virtually indistinguishable from the other female characters; post- ArtEvolution his only barely male noticeable trait is being taller than other policewomen.
** While Aoi's actual taste in partners doesn't come up much, one episode does have him seemingly worried a recent male E-friend will find out he's not actually a woman. Most fans simply assume [[UnfortunateImplications this simply because of the common okama stereotypes]].
** Aoi is more of a {{Transsexual}} then a simple crossdresser though.
* A running joke in ''KokoWaGreenwood'' (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 ''IMyMeStrawberryEggs'', 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 ''FushigiYuugi''. His actual gender is revealed pretty early on in the series.
** {{Bishounen}} Hotohori, while usually just [[DudeLooksLikeALady mistaken to be a woman]] (especially by Miaka during their first meeting), with minimal effort he has on occasion been a WholesomeCrossdresser . 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 {{WholesomeCrossdresser}}s (he and Nuriko were the only men convincingly looking like women, to the chagrin of the others).
* Like her VideoGame [[VideoGame/{{Persona 4}} counterpart]] [[spoiler: Naoto Shirogane]] of ''Anime/Persona4TheAnimation'' is one of these.
* ''Manga/OuranHighSchoolHostClub'' 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 WholesomeCrossdresser, who works at an [[HostClub 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 ''OtomeWaBokuNiKoishiteru''. 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.
* Alice in ''LightNovel/MariaSamaGaMiteru''.
* Ciel from ''Manga/BlackButler''. In episode 4 of the anime, he sneaks into a ball in a very...[[http://www.cosplayisland.co.uk/files/costumes/85/10923/kuroshitsuji2020042020lgv1.jpg 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 [[http://www.mooncostumes.com/image/26849 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 [[AttractiveBentGender 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 VisualNovel, he's effectively the GayOption [[spoiler:although 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 ''Manga/RanmaOneHalf'', 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 MasterOfDisguise 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 [[SweetOnPollyOliver fooled by her disguise]]).
** Later in the manga, Ranma, Ryoga, and a couple other characters must distract the [[{{Orochi}} Yamata No Orochi]], which has a taste for women. Therefore, they (as men, even [[GenderBender 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 [[SleevesAreForWimps Chinese uniform]] he [[LimitedWardrobe 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.
* ''RevolutionaryGirlUtena'''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 PrinceCharming.
* In the ''{{Mai-Otome}}'' manga, Princess Mashiro is replaced by her twin brother. The gags of the manga constantly poke fun at "[[FanNickname Manshiro's]]" plight.
* Randoh/Yuna from ''PrettyFace''.
** Justified/handwaved in that he was ''[[LongStory surgically rebuilt from a disfigured near-corpse to look like a teenaged girl]]''.
* Seki from ''Manga/DokiDokiSchoolHours'' likes to dress up in womens' attire - actually hoping he will impress ''girls'' that way.
* From ''LightNovel/KinosJourney'' is [[spoiler:Kino. She is still young, but her gender is fairly ambiguous to most characters, and they tend to refer to her using male pronouns.]] Even [[{{Bokukko}} she does this herself]] sometimes. The anime also doesn't make a point of [[ViewerGenderConfusion clarifying the matter to the viewer]] until episode 4, [[spoiler:eventually revealed to be the story of how her journey began]].
* ''ShugoChara'' has [[spoiler: 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 [[DoubleStandard polearm-wielding maniac]], similar to Tadase's ironic change, and not swimming. Interestingly, she is PutOnABus 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 CastFullOfPrettyBoys in regards to the 'normal characters', with her Chara teasing Amu's habit of crushing on every - one.
* Makoto/"Mako-chan" in ''Manga/MinamiKe''. [[ClarkKenting 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.
* Yellow Belmont from ''{{MOSPEADA}}'' (Lancer/Yellow Dancer in ''{{Robotech}}'').
* In several episodes of ''Manga/HayateTheCombatButler'', 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 MoeMoe 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 [[spoiler: 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 [[RecursiveCrossdressing girl who likes to wear boys cloths.]] ]] How well Hayate fits here is even a bit of a RunningGag in the manga.
* ''FruitsBasket'' 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 [[spoiler:Akito]]: shortly after we learn they are a VillainousCrossdresser, 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.
* Hamaji in ''VisualNovel/H2OFootprintsInTheSand'', who ends up [[spoiler:marrying his best (female) friend, fathers a child]], and still dresses like a girl.
* There's quite a few of these in ''FamilyCompo'' -- 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 [[WillTheyOrWontThey 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 ''PenguinRevolution'' are {{Wholesome Crossdresser}}s. 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. HilarityEnsues.
* Racine Blanche Volban in ''GlassFleet'' 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 StalkerWithACrush, who is [[UnsettlingGenderReveal a bit put out when he discovers that "Michel" is a woman]].
* Nagisa and Ryunosuke from ''UruseiYatsura'', 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 ''NoBra'' is a sweet, kind, beautiful and roommate Masato Kataoka's perfect girl. [[HoYay Except she's a he]].
* Ayase from ''OkaneGaNai'' 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. [[BoysLove In his case]] it might not be all that surprising that this earns him a severe [[StalkerWithACrush stalker]] who is not bothered to learn his real gender and proceeds to stalk him anyway.
* ''Franchise/{{Gundam}}'' examples:
** Loran Cehack's female alter-ego Laura Rolla in ''Anime/TurnAGundam''.
** In a possible homage to Laura Rolla, ''[[Anime/MobileSuitGundam00 Gundam 00]]'''s [[spoiler: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 [[spoiler:he can sneak into a high class party and speak to Ribbons. And to make fangirls melt into a collective puddle over [[StupidSexyFlanders Stupid Sexy Girl!Tieria]], while several fanboys went "[[EvenTheGuysWantHim TIERIA IS A MAN AND HE'S OURS!]]".]]
* Alto Saotome from ''MacrossFrontier'' 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 {{Lampshade}}d by his friends, who often tease him and call him "Princess Alto" due to his appearance. People who don't know Alto [[UnsettlingGenderReveal 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 [[spoiler: dresses up as a [[{{Meido}} maid]]]].
* In ''Manga/FairyTail'', 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. [[spoiler: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 ''Manga/JoJosBizarreAdventure''. 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. HilarityEnsues.
** 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 [[AxCrazy 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 VillainousCrossdresser, 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. [[spoiler:Then towards the end of the series, we find out that Sandman's BattleButler was Eiji's missing sister the whole time, so it seems to run in the family.]]
* Yozak from ''KyouKaraMaou'', though taller and more muscular than his fellow bishounen, loves to disguise himself as a woman. A cheerfully flirtatious woman, even.
* ''MahouSenseiNegima'' combines this with InstantCosplaySurprise, with the girls dressing Negi up as a surprisingly cute fox girl. It sure gave [[{{Shotacon}} Ayaka]] a massive [[TheNosebleed nosebleed]].
** ''Negima?! Neo'' gives us Cheerleader Negi in chapter 19. [[http://static.tvtropes.org/pmwiki/pub/images/Cheerleader_Negi_2668.JPG As seen here, he's not the only one in drag (hint: the other one's wearing bandages around her chest).]]
* In ''VisualNovel/{{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.
* Hans of ''Manga/TheDaughterOfTwentyFaces'' does this, albeit unwillingly, for a circus act the nakama are producing in episode 5 of the anime.
* ''TokyoGodfathers''' 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 [[DoorstopBaby Trash Bin Baby]] to heart. Has an extremely GirlyRun and a bass voice.
* [[spoiler:Kei]] from ''[[{{Zeiram}} Iria:Zeiram]]''.
* Husky from ''Manga/PlusAnima'' 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 [[spoiler:kidnapped and sold as a slave in Sailand]], he dresses up like a girl [[spoiler: so he'll sell for a higher price.]] Cooro and Nana come to [[spoiler: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.
* ''OnePiece'' examples:
** The Kamabakka Kingdom is, quite literally, "full of transvestites". Even the ''[[http://www.onemanga.com/One_Piece/523/18/ 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 [[{{Squick}} squicking]] out Sanji, so YMMV on the wholesome part.
** [[http://randomc.net/image/One%20Piece/One%20Piece%20-%20454%20-%20Large%2016.jpg Sanji]] was humiliated and tricked into becoming a crossdresser himself. Fortunately, he got better.
* In the original ''Manga/SailorMoon'' manga, Creator/NaokoTakeuchi 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/SailorMoon 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.
* ''WJuliet'' has Makoto Narita, the male lead, who dresses as a woman [[spoiler: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 [[spoiler: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).
* Kiri in the manga ''NeverGiveUp'' [[{{Bifauxnen}} 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 [[EvenTheGirlsWantHer half the school's female population from developing huge crushes on her]]. However, in order to stay close to her love interest, the [[{{Bishounen}} effeminate]] Tohya, she has to sign a modeling contract. As a ''male'' model.
* Keiichi in ''VisualNovel/HigurashiNoNakuKoroNi'' 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.
* Noto Kanazawa aka Noto-sama, created by ''AxisPowersHetalia'''s author HidekazHimaruya and the star of the short manga ''Advance! Kitakou Broadcasting Club''. He's a cross-dressing SchoolNewspaperNewshound who's often found [[NakedPeopleAreFunny stripping other people]] with his partner-in-crime, [[LovableSexManiac Yamato]] [[{{Delinquents}} 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 OrdinaryHighSchoolStudent and a bit of a ButtMonkey, as well as being [[NiceGuy much less pushy]]. After the series added ''Pure'' to its title and Himaruya started drawing ''Barjona'', Noto was revealed to be CuteAndPsycho and snapped, starting on the path to his current incarnation. This era of the comic was taken off the website though, presumably due to OldShame.
** 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.
** As for ''Hetalia'' itself, Poland has dressed up in girls' clothes (usually miniskirts) in a few strips, which tends to weird out his [[HeterosexualLifePartners Heterosexual Life Partner]] ([[HoYay 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 HistoricalInJoke.
** As of HetaliaBloodbath2010, 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 RaisedAsTheOppositeGender 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 ''LightNovel/{{Sukisho}}'' is never explicitly discussed, his clothing is mostly [[AmbiguousGender 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 ''MidoriNoHibi'' 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 ''PrunusGirl'' is very convincing, but helpfully reminds everyone at least once a chapter that he's a guy in between teasing Maki and hinting at RecursiveCrossdressing.
* Haku from ''Manga/{{Naruto}}'' is on the borderline between WholesomeCrossdresser and VillainousCrossdresser being that he's an AntiVillain.
** From the fillers, there's Princess Toki of the Land of Birds, who is also impersonating her dead brother Sagi.
* ''Manga/ButterfliesFlowers'': Domoto's coworker and very ''close'' friend [[spoiler:Suou, of whom Choko is quite jealous]] until she realizes he's a ''he''.
* Used as a one-off gag in ''GameXRush'', 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, [[ViewerGenderConfusion 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 [[FanGirl love]] for the extremely girly Idol Band, Eclipse.
* Reborn of ''Manga/KatekyoHitmanReborn''. Then again, he's a baby, so he can get away with it.
* Miyashita Masashi from ''[[OniichanToIssho Onii-chan to Issho]]'' (official English title: ''[[OniichanToIssho 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'' [[WholesomeCrossdresser crossdresses]] and {{Cosplay}}s 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 [[spoiler: 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 Anime/{{Pokemon}} has to dress as "Ashley" to get his Gym battle with Erika. [[LoveableSexManiac 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 ''Manga/{{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.
* ''LightNovel/BakaToTestToShoukanjuu'''s Hideyoshi is one, naturally. But since he has an identical twin sister, the cast and us can let it slide. [[BaitAndSwitchComparison The fact]] [[StupidSexyFlanders that Hideyoshi's a boy]], that is.
* ''{{Nononono}}'' is a ski-jumping manga by the author of ''Manga/ElfenLied''. 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 ([[InsistentTerminology Seiko]]!) from LovelyComplex is very nice and friendly (a little [[UnsettlingGenderReveal TOO friendly]] with Ootani) who insists "god made a mistake" and put her into a boy's body. After TheReveal 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 [[HoYay by way]] [[{{Tsundere}} of]] [[LongHairedPrettyboy Haruka]]), Seiko seems to fit in and find a happy school life with little difficulty.
* In ''Manga/TheWorldGodOnlyKnows'' Yui Goudou started doing this after [[FreakyFridayFlip 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!
* Fay in ''TsubasaReservoirChronicle'' sometimes does this. In the AlternateUniverse 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 [[Manga/XxxHOLiC 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[[/note]] 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 ''TsubasaReservoirChronicle'' are worn in a masculine fashion; however, they are identifiable as furisodes due to the sleeve length.
* Levin from ''Anime/TekkamanBlade''.
* Ayumu from ''KoreWaZombieDesuKa'', as he's drafted into a ''MagicalGirl'' army after his zombie nature absorbs most of Haruna's powers, including the ability to transform into a Masou Shoujo.
* Sister from ''ArakawaUnderTheBridge''. The man wears a nun's habit for day-to-day life and on one occasion donned a schoolgirl uniform.
* A number of transvestites appeared in "Jupiter Jazz", an episode of ''Anime/CowboyBebop''. One of them even returned for TheMovie.
* In ''Manga/FullmetalAlchemist'', 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 [[AmbiguouslyGay frequently flirts with Ed and other male characters]].
** Lt. General Grumman disguises himself as an old woman at one point to meet with Mustang.
* ''WanderingSon'' 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 CoolBigSis 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 [[{{Meganekko}} isn't a bad thing]]). Chizuru is a girl who sometimes crossdresses as a boy, and she looks like androgynous.
* Oscar from ''RoseOfVersailles'' is another example of the girl-raised-as-a-boy plot device.
* Makoto Mizuhara from ''Anime/ElHazardTheMagnificentWorld'', Yakumo from ''Manga/SazanEyes'' and Yellow Belmont aka Lancer from ''Genesis Clumber Mospeada''/''Robotech Third Generation'' crossdress as a plot necessity rather than for their personal tastes. I.e.: Lancer crossdresses and poses as a female IdolSinger to act as a spy for [[LaResistance the resistance group]] he's a part of.
* All of the "princesses" in ''PrincessPrincess''.
* The tenants, particularly Yuki, frequently dress up as women for various convoluted reasons in ''TheWallflower''.
* LightNovel/{{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 ''GetBackers''. 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 [[LampshadeHanging 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.
* ''Manga/{{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 [[spoiler: Yagyuu Kyuubei]].
* ''Manga/{{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 ''Manga/BlackCat'' 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.
* ''Anime/NeonGenesisEvangelion'''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.
** In ''ShinjiIkariRaisingProject'', Asuka and Rei find him even more attractive when he is forced to wear a dress. Do they get a bonus point for LesYay?
* Yozak from ''LightNovel/KyoKaraMaoh'' 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.
* Ryo Hayama of ''Bremen'' fully dresses up as a girl which includes wigs, fake boobs, platform shoes, [[FemmeFatalons fake nails]], etc. [[BerserkButton Just beware about calling him one]].
* 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 ''ThereBeyondTheBeyond'', Futaba admits that wearing girly clothes doesn't bother him, because his older sister makes him do it all the time.
* From ''[[Manga/{{Plus-Si}} +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 [[DisguisedinDrag disguise]], it appears that yes, they're very much this trope. In his youth, Eco apparently went out to drag contests, and [[spoiler: 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 ''Manga/UsotsukiLily'' 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. HilarityEnsues 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 ''Manga/YuYuHakusho''. 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.
* ''Manga/MaidSama'': Aoi Hyoudou.
** 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.
* G in ''FromEroicaWithLove''.
* Shizu in ''MariaHolic''. 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, LightNovel/HaruhiSuzumiya has her moment when she's allegedly DisguisedInDrag in chapter 3 of ''Disappearance''.
* In ''OhEdoRocket'' 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 [[ShowWithinAShow 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 ''Literature/OtokoNoKoWaMeidoFukuGaOsuki'' are four brothers who help their parents' MaidCafe, 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 ''KunisakiIzumoNoJijou'', who is already [[DudeLooksLikeALady 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.
* Kou From ''Manga/SamuraiHighSchool''.
* Fire Emblem from ''TigerAndBunny'' loves his pink angora, high heels, and makeup. He's also a successful [[CorporateSponsoredSuperhero Hero]] with [[PlayingWithFire fire-based superpowers]], is the CEO of a major corporation, and acts as TeamMom for the rest of the cast.
* [[PunnyName Anna Graham]] of ''Anime/PhiBrainPuzzleOfGod'' is an ''extremely'' girly boy, to the point that [[TheHero 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 FriendToAllLivingThings turned UpToEleven.
* Minoru in ''Manga/AKB49RenaiKinshiJourei'' 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 ''Manga/{{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 ''HeartcatchPrettyCure'' 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 DistantFinale wearing the school's female school uniform.
* Out of all the characters in ''{{Franchise/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.
* Kotarou from ''DenpaKyoushi''. [[http://www.mangahere.com/manga/denpa_kyoushi/c045/7.html So feminine he was banned from wearing the male uniform.]]
* Ayumu Mikoshiba from ''Manga/OtasukeMikoMikoChan'' is one, however reluctantly. A character introduced later, though, has no such qualms about cross-dressing.
* In ''HidanNoAria'', this is [[spoiler:Kinji's brother]]'s method to activate Hysteria Mode (which is triggered by sexual arousal). The result is so convincing that Aria thinks [[spoiler:Kana is Kinji's ex-girlfriend.]] And it actually seems to create a SplitPersonality − at least according to Kinji, [[spoiler:Kana and his brother]] are "different personnas". You can't get more "wholesome" than that.
* [[TheHero Shinobu Nanjou]] and [[BromanticFoil Kouta Asada]] in ''LightNovel/TsukiTsuki'' are forced to wear a maid and a Chinese dress at the sports festival. [[http://i39.tinypic.com/2ebg9qb.jpg It's very convincing.]]
* Natsume, from ''LightNovel/TokyoRavens'' dresses as a boy in public.
* Hime, from ''Manga/{{Himegoto}}'', is forced to dress as a girl during school. In the spinoff ''Himegoto+'', ''everyone'' in the main cast cross-dresses.
[[/folder]]

[[folder:Comic Books]]
* 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 [[HarmlessLadyDisguise harmless-seeming old lady]] after his daughter was kidnapped. Because no-one suspects the old lady.
* And then there's [[Comicbook/{{Empowered}} the Goddamn Maidman!]]
* {{Superman}}'s Pal JimmyOlsen has disguised himself as a woman... [[http://www.tgfa.org/comics/jimmy_olsen/jimmy_olsen.htm more than a few times]], actually. He's rather good at it.
* George (who is either a crossdressing woman or a transgender man, the comic never elaborates) in Creator/GrantMorrison's ''Sebastian O'' is one of the more sympathetic characters in the comic. Not that the bar is particularly high.
* Lord Fanny in Creator/GrantMorrison's ''TheInvisibles'', who was raised as a girl by her grandmother, a witch, because men could not become witches.
* Danny the Street, in Creator/GrantMorrison's (sensing a theme here?) ''Comicbook/DoomPatrol'', is a transvestite sentient street.
* Sir Ystin, the Shining Knight from ''ComicBook/SevenSoldiers'' (and yet another Morrison creation) is a girl disguised as a boy. The New 52 version seen in ''ComicBook/DemonKnights'' is [[GenderBender a different matter]]...
[[/folder]]

[[folder:Fan Fic]]
* Both Mitsuuru Takahashi and Shugo Kino in FanFic/PrettyCureHeavyMetal are this, with the only exception being when they're attending Isuten Junior High. Outside of school, Shugo takes the RealWomenNeverWearDresses 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 ''[[FanFic/PrettyCureAllStars 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 ''Manga/CardcaptorSakura'' (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 SuzumiyaHaruhi (in that play, Shugo portrayed Kyon).
* Harveste Addams of the [[http://www.fanfiction.net/s/6341291/1/ 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 ''[[FanFic/SuzumiyaHaruhiNoSeitenkan The Melancholy of Haruki Suzumiya]]'', Haruki has Mitsuru wear a maid outfit for a photo shoot.
* In the ''Hooker Verse'', WebVideo/TheNostalgiaCritic wears a corset and skirt. Of course, the 'wholesome' part is a little debatable given that he's, well, a [[ExactlyWhatItSaysOnTheTin hooker]], but...
* In one ''Anime/NeonGenesisEvangelion'' 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 [[HoYay 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 ''FanFic/ADayIndoors''. Negi wonders if the frilly pink panties were necessary, really. Yuuna certainly seems to think they are.
[[/folder]]

[[folder:Film]]
* All three protagonists of ''TheAdventuresOfPriscillaQueenOfTheDesert'', to varying degrees. Creator/TerrenceStamp plays a hard-drinking but patient transsexual, Creator/GuyPearce a bitchy, high-strung PerformanceArtist, and Creator/HugoWeaving is the [[ShrinkingViolet 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.
* ''Film/ToWongFooThanksForEverythingJulieNewmar'' has Creator/JohnLeguizamo, Creator/PatrickSwayze, and ''[[WTHCastingAgency Wesley Snipes]]'' all as crossdressing drag queens. Vida and [[OddNameOut Noxeema]] even convince Chi-Chi to give up the boy she has a crush on to the girl in town that likes him, as it [[UnsettlingGenderReveal wouldn't be fair to him]].
* TheFifties comedy film ''SomeLikeItHot''. Originally Joe and Jerry did it to escape TheMafia, but they kept up the act... and Jerry [[IfItsYouItsOkay took his new role very seriously]].
* In Takashi Kitano's ''Franchise/{{Zatoichi}}'', Geisha Seitaro 'Osei' Naruto is actualy a man.
* ''{{Tootsie}}''. While Dustin Hoffman starts out playing a woman simply in order to get work, he ends up playing the part in real-life as well.
* In ''Literature/{{Trainspotting}}'', Begbie makes out with a "woman" in his car for a while before discovering it's a man.
* Kitten from ''BreakfastOnPluto'' (played by Cillian Murphy) basically personifies [[TheCutie "cute"]].
* Roger [=DeBris=] from ''Film/TheProducers''.
-->"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 ''Film/EdWood'': 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.
* This was also how Creator/EdWood portrayed [[AuthorAvatar a thinly-disguised version of himself]] in ''GlenOrGlenda''.
* One of the "edgy" things about Baz Luhrmann's modern remake of ''Theatre/RomeoAndJuliet'' is having Mercutio (played by [[Series/{{Lost}} Harold]] [[Film/TheMatrix 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 [[AmbiguouslyGay Mercutio.]]
** And he also dances and lip-syncs to "Young Hearts Run Free". It's awesome.
* Vilma in ''TakingWoodstock''.
* 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 Music/BarbraStreisand".
* In both the film and the play of ''VictorVictoria'', 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 RecursiveCrossdressing.
* Saga in ''Mitt liv som hund'' (My Life as a Dog).
* In ''DonJuanDemarco'', the title character (played by JohnnyDepp) 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 ([[http://www.deppimpact.com/gallery/albums/caps_djd/djd386.JPG 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 ''Literature/DonJuan''.)
* In ''Film/WaitingForGuffman'', director Corky St. Clair might be a closeted example. He often buys clothes for his wife Bonnie, a reclusive lady [[GirlfriendInCanada who nobody ever seems to have met]].
* 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 ''Film/SwissFamilyRobinson'' had Roberta, who was disguised as a cabin boy by her father to protect her from the pirates.
* In ''KinkyBoots'' 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.'

[[/folder]]

[[folder:Literature]]
* George, from the otherwise hilariously backward children's series ''Literature/TheFamousFive'' 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 ''WelkinWeasels: 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".
* [[spoiler:Éowyn, so she can fight in the final battle,]] from ''Literature/TheLordOfTheRings''
* OlderThanPrint: 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 [[LesYay kisses the Greek princess Nura]].
* In ''Literature/TheWalkerPapers'' series by C.E. Murphy, Joanne's friend [[UnfortunateNames Billy Holiday]] is a crossdresser who is also a respected police detective and happily married with children.
* Terence, the squire in Gerald Morris's ''TheSquiresTales'', crossdresses to help rescue Sir Gawain from a dungeon.
* Louis from ''Literature/TheExtraMan'' [[spoiler:until he decides it's not for him]].
* Alanna from ''Literature/SongOfTheLioness''. During her time, girls were not allowed to be knights so she had disguise as one to receive training.
* Sally Sweet in the StephaniePlum series. He's described as not exactly attractive and nearly every other sentence out of his mouth is a ClusterFBomb, 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 ''EvilGeniusTrilogy'' 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 Creator/{{CLAMP}}'s light novel series ''CLAMP School Paranormal Investigators'' is a boy who dreams of becoming a famous actress. To that end, [[spoiler:he wears the girls' school uniform]].
* Even after she's stopped performing in the music halls in drag, TheProtagonist Nan of ''Literature/TippingTheVelvet'' is more comfortable in men's clothing and continues to wear her costumes.
* ''Literature/SongAtDawn'' [[spoiler: '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 ''Literature/CallahansCrosstimeSaloon'' 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.
* ''Literature/{{Theatrica}}'' with the character Vivian.
* This is of course a core theme of TerryPratchett's novel MonstrousRegiment.
* Pulaski, the cross-dressing killing machine in ''Literature/UndeadOnArrival'', is one of the more heroic characters in the novel. He's the most fabulous by a large margin.
[[/folder]]

[[folder:Live-Action TV]]

* ''BoyMeetsWorld'' 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 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 ''MyBabysittersAVampire'' 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 ''Series/{{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 ''HillStreetBlues,'' 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 ''TwinPeaks'', played by David Duchovny. (Who, as it turns out, has ''[[AttractiveBentGender really nice legs]]''.) Also a rare case of a heterosexual crossdresser on network TV.
* Reality TV example: Derrick Barry of ''AmericasGotTalent''
* Clarence from ''BostonLegal'' crossdressed as both an alter ego, Clarice, and ''Oprah''.
* Drew Carey's brother on ''TheDrewCareyShow'', before marrying Mimi.
* Subverted in ''LeaveItToBeaver'', 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 ''Series/AreYouBeingServed''. 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 ''Series/GetSmart'', is such an exceptional undercover agent that he looks exactly like the RealLife (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 Series/MythBusters, Tory wore a bra ForScience. Another time, while re-enacting a scene from Film/{{Speed}}, he wore a wig. "Once again, making my parents proud."
* In a BBC modern-dress production of ''Theatre/TheTamingOfTheShrew'', Petruchio was a rare Western media example of a heterosexual crossdresser.
* This is a common occurence in ''Franchise/SuperSentai'' series:
** In an episode of ''Series/DaiSentaiGoggleFive'' that featured dolls coming to life, [[MasterOfDisguise 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 [[KnightInShiningArmor handsome prince]] disguise via a wig and a fitting outfit.
** Then, in ''Series/ChoujinSentaiJetman'', the one cross-dressing was... [[TheBigGuy Raita/Yellow Owl]], in order to trick a MonsterOfTheWeek 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 ''Series/HyakujuuSentaiGaoranger'' also pulled off cross-dressing as a bride. Even if he ended up striking the sumo pose and "Dosukoi!" yell.
** Tetsu/[=DekaBreak=] in ''Series/TokusouSentaiDekaranger'' 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 [[MemeticMutation 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 ''Series/SamuraiSentaiShinkenger'', with [[LargeHam 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 {{Bishonen}} 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. [[SugarWiki/FunnyMoments 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 ''[[Series/ThirtyRock 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[[/note]]
* British soap ''Series/{{Hollyoaks}}'' features Kris, a bisexual cross-dressing man.
* Dave in ''Series/{{Degrassi}}'' wore a long frilly skirt to prove a point when [[{{Transgender}} Adam]] made him uncomfortable.
* ''CoronationStreet'', 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 ''Series/BosomBuddies'' was DisguisedInDrag, but the boys carry on with the charade over the course of the series longer than seems strictly necessary.
* ''{{Series/Wallander}}'' offers us [[spoiler: Louise, Kalle Svedberg]]'s girlfriend.
* Jodie from ''Series/{{Soap}}'' dresses as a woman a few times during his "I want to be a woman" phase in season one.
* In ''Series/{{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.
* Wade "Unique" Adams from ''Series/{{Glee}}''; ShrinkingViolet as a boy, SassyBlackWoman as a girl.
* One of the many subplots in one of the first-season episodes of ''Series/{{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.
[[/folder]]

[[folder:Manhua]]
* Xiao Meng the eunuch assassin from Chinese {{manhua}} ''Manhua/RavagesOfTime'' insists he's a man, but specializes in disguising himself as a woman.
[[/folder]]

[[folder:Music]]
* The protagonist of the song "Cherry Lips" by Garbage.
* "Lola" by Music/TheKinks.
* Desmond, the family man who "stays at home and does his pretty face" in "Ob-La-Di, Ob-La-Da" by Music/TheBeatles. Funnily enough, that lyric was a mistake made by Paul, but they [[ThrowItIn left it in]] because they were sick of working on that song.
* Pretty much everyone in Music/{{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!''"
* Music/GreenDay's "King for a Day" (Princess by dawn!).
-->"''Who put the drag in drag queen?\\
Don't knock it until you've tried it''"
* [[Music/{{Vocaloid}} Kagamine Len]] is this in "Imitation Black" and other VisualKei styled songs by natsuP. He arguably is in "Servant of Evil," [[spoiler: despite the title, he's a LoveMartyr who crossdresses to pull a TwinSwitch to keep his evil sister from being beheaded.]]
** Kaito in "The Madness of the Duke of Venomania" does this [[spoiler: to trick and kill Gakupo, who's been luring innocent women into his harem.]]
** The UTAU Ritsu Namine.
* The protagonist of Music/{{Placebo}}'s song "Nancy Boy".
* "Rosie" by Joan Armatrading.
* [[Music/FlorenceAndTheMachine Florence Welch]] wears a suit both in the 2008 video for "Dog Days Are Over", and in the "Sweet Nothing" video.
[[/folder]]

[[folder:Mythology]]
* Lan Caihe of the [[ChineseMythology Eight Immortals]] may or may not be one. [[DependingOnTheWriter It depends on who you ask.]]
* According to some versions of the Minotaur's story, [[ClassicalMythology Theseus]] decides to switch two of the seven female victims with [[AgentPeacock 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 [[http://www.youtube.com/watch?v=Ha1dFpiVe58 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.
* In one of the most well loved of the [[NorseMythology Norse Myths]], Thor dons a full wedding gown in order to disguise himself as Freyja. ItMakesSenseInContext.
[[/folder]]

[[folder:Religion]]
* [[Literature/TheBible Deuteronomy 22:5]] defies this trope severely:
-->''"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."''
[[/folder]]

[[folder: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.
** 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 [[UnsettlingGenderReveal in order to avoid confusion]].
* The Howling Banshee's, an Eldar class in ''{{Warhammer 40K}}'' are traditionally an [[AmazonBrigade 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'.
[[/folder]]

[[folder:Theater]]
* Creator/WilliamShakespeare's comedies employ this trope rather often, partly owing to the nature of Elizabethan theatre in general. Women weren't allowed on stage by law, so female roles were played by male actors. Thus, when a female character is a WholesomeCrossdresser, as in ''Theatre/TwelfthNight'', she would have been played by a [[RecursiveCrossdressing man playing a woman dressed as a man]]. The trope is taken even further in ''AsYouLikeIt'', where Rosalind would have been a man playing a girl disguised as a boy pretending to be a girl.
** 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.)
* ''[[LaCageAuxFolles La Cage Aux Folles]]''.
* Angel Dumott Schunard from ''Theatre/{{Rent}}'', who may also be {{Transsexual}}.
* Fancourt forced to chaperone as the titular ''Charlie's Aunt.''
[[/folder]]

[[folder:Video Games]]
* Bridget from ''VideoGame/GuiltyGear''. 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 [[ScrewDestiny 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.
** A [[MemeticMutation common]] ImageMacro used for {{Troll}}ing shows a picture of him and says "[[EvenTheGuysWantHim Everyone's gay for Bridget]]". Very confusing if you haven't played the game. There's a reason UnsettlingGenderReveal used to be called "Dropped A Bridget On Him".
** Despite his mannerisms and [[{{Fanservice}} the promo art]] [[TrollingCreator featuring 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.
* ''VideoGame/{{Persona 4}}'' [[spoiler:Naoto is a woman masquerading as a man.]]
** Another example would be [[spoiler:Human Teddie, who can pull off cosplaying Literature/{{Alice|InWonderland}}.]] Yu and Yosuke in the crossdressing pageant could count too, but the student body has [[CreepyCrossdresser 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 ''VideoGame/{{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 ''VideoGame/FinalFantasyV''. [[BraggartBoss 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 [[UnsettlingGenderReveal 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 [[spoiler: 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 StupidSexyFlanders moment, [[spoiler:from how they got surprised of the revelation. They still called her a guy after that scene, anyway.]]
* In ''VideoGame/FinalFantasyVII'', hero Cloud Strife has to rely on the help of some friendly transvestites so that he can [[DisguisedInDrag disguise himself as a woman]] and infiltrate a gangster's mansion.
* From ''SuikodenV'', [[spoiler:[[DragonRider Rahal]] dresses up as his sister to distract some guards. [[AttractiveBentGender Those guards were not the only ones distracted]]; he [[HalfIdenticalTwins looks]] ''[[HalfIdenticalTwins exactly]]'' [[HalfIdenticalTwins like his sister]] when wearing her dress and hairstyle.]]
* In ''[[VideoGame/PokemonGoldAndSilver 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.
** One of the Ferris Wheel date options for the male player character in ''VideoGame/PokemonBlack2AndWhite2'' is a schoolteacher who, in the Japanese version only, [[UnsettlingGenderReveal 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 Gardevior's DistaffCounterpart, Gallade. Even in Gen IV and beyond, it's still perfectly possible to have a male Gardevior, since Gallade uses a different evolution method[[hottip:*:a Dawn Stone instead of leveling up]].
** Similarly, Lopunny is based on a PlayboyBunny, 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.
* ''VideoGame/AnimalCrossing'' examples:
** 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 GirlyRun 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".
** Gracie the giraffe fashion designer and Saharah the camel who trades in carpets and wallpaper [[ShesAManInJapan are both guys in the Japanese versions]].
* ''VideoGame/LeisureSuitLarry'':
** 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.
* ''DeathSmiles II'' features Lei, who is a twelve year old boy wearing an ElegantGothicLolita 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).
* Mike in ''VideoGame/StarTropics'' crossdresses ([[GenderBender or maybe magically changes gender]]) to enter an all-female village.
* In ''[[KunioKun 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 [[ImScaredOfGirls I'm Scared of Girls]].
* In ''VideoGame/TalesOfVesperia'', 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 [[VideoGame/TalesOfRebirth Mao]] and [[VideoGame/TalesOfLegendia Walter]] available for her to wear.
** Milla from ''VideoGame/TalesOfXillia'' can wear the costumes of [[VideoGame/TalesOfDestiny Stahn]] and [[VideoGame/TalesOfPhantasia Dhaos]]. She also has access to [[VideoGame/TalesOfGraces Asbel's]] costume in ''VideoGame/TalesOfXillia2''
* Daphnis in ''VideoGame/TearsToTiara2'' crossdresses so he can follow [[TheOjou 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.
* ''VideoGame/SouthParkTheStickOfTruth'' has JustForFun/PrincessKenny, 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 [=LARP=]ing dress and a bad wig. She holds up the "wholesome" by fighting at [[PlayerCharacter the New Kid's]] side [[spoiler:until her FaceHeelTurn, when she becomes the FinalBoss.]]
** The New Kid can also end up crossdressing after a makeover from the Girls. There's a secret achievement for [[spoiler:wearing the get-up while fighting Princess Kenny.]]
[[/folder]]

[[folder:Visual Novels]]
* ''VisualNovel/MajiDeWatashiNiKoiShinasai'' has Moro who occasionally has had to suffer the indignity of [[AttractiveBentGender crossdressing]] for some greater cause. Some members of the family would rather him do it more often.
* Saber aka [[spoiler: KingArthur]] from VisualNovel/FateStayNight. And in the {{Prequel}} FateZero she dresses as a businessman.
* Ryouta Kawara tends to show up in girls' outfits at various points in ''VisualNovel/HatofulBoyfriend''. 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 [[VictoriousChildhoodFriend canon love interest]].
** If you follow Ryouta's path in the full version, he [[JustifiedTrope 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 MagicalGirl, 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 ''VisualNovel/KiraKira'', 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 ''Franchise/{{Angelique}}'' series of dating sims for girls. Yes, he is a possible love interest in every game he appears in.
* [[spoiler:Sayo Yasuda, also known as Shannon, Kanon and Beatrice]] from ''VisualNovel/UminekoWhenTheyCry'' is implied to be this in one direction or another. Of course, because [[spoiler:Yasu]]'s gender [[AmbiguousGender 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 [[spoiler:Sayo was a biologically male child who was RaisedAsTheOppositeGender]].
* [[spoiler:Chihiro Fujisaki]] from ''VisualNovel/DanganRonpa''.
[[/folder]]

[[folder:Web Comics]]
* Tip Wilkins from ''SkinHorse'' is a cheerful TheCasanova 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 ''Literature/LandOfOz'' motif, specifically to [[spoiler:Princess Ozma]].
* Magical Transvestite Cherry from ''{{Webcomic/Footloose}}'', described on the cast page as "the only MagicalGirl with a [[GirlPosse shred of humanity]]."
* Paul "the transvestite stalker" from ''Webcomic/CollegeRoomiesFromHell!!!'' - 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 RunningGag, serving as the voice of reason essentially whenever he plays a significant role.
* ''MaterialGirl'' features a teenager ''forced'' into this.
* 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 ''Webcomic/ElGoonishShive'' when avowed pervert (and frequent GenderBender) 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.
* Dana and other Elle-Boys in the ''Webcomic/JetDream'' RemixComic always dress as females, but are fairly chaste and strictly heterosexual, apparently due to the (fictional) publisher's misguided attempt to pass UsefulNotes/TheComicsCode and/or [[AuthorAppeal Publisher Appeal]].
* 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 UmlautHouse 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).
* [[http://www.girlswithslingshots.com/comic/gws9/ Darren]] from ''WebComic/GirlsWithSlingshots.''
* Red Mage, the delusional {{Munchkin}} of [[WebComic/EightBitTheater 8-Bit Theater]] has a tendency to cross dress and pretend to be a woman named Deborah. He [[FreudianExcuse blames his father]] for this, but Thief states that he himself managed to put those memories into Red Mage's mind somehow.
** Obviously, he [[IncrediblyLamePun stole them into it]].
* In the ''{{Insecticomics}}'', the Insecticons are fond of donning Barbie dresses, and actually look quite good in them. It's hilarious. "[[DoesThisMakeMeLookFat Does this dress make me look fat]], [[VerbalTic 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 ChaoticNeutral.
* Toadsuke from ''SupahNarioBros''.
* [[AnneOfGreenGables Green Gable]] from ''{{Spinnerette}}'' is the first male to [[LegacyCharacter 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 RealMenWearPink, 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!
* It appears in ''DoubleK'' that nearly 90% of Kamina's plans involve [[http://doublek.thewebcomic.com/comics/1358248/chapter-1-03/ putting]] [[http://doublek.thewebcomic.com/comics/1373038/chapter-3-064/ Simon]] [[http://doublek.thewebcomic.com/comics/1373039/chapter-3-071/ in drag]].
* In ''Webcomic/WelcomeToRoom305'' there's [[spoiler:Yoon Sung]], who likes to dress up as a woman at night. [[spoiler:Subverted when it's revealed that it's actually his twin sister]].
* In MoonCrest24, 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 [[BlandNameProduct Cool Topic]] to get him actual (emo) boy clothes.
* In ''Webcomic/QueenOfWands'', Felix occasionally crossdresses, and nobody makes a big deal about it.
* [[ThePaladin Alec]] in ''Webcomic/CastlevaniaRPG''
-->'''Cassandra Belmont:''' He [[http://www.cvrpg.com/archive/2012/08/28 makes]] a better looking woman than I do.
* Jane from ''{{Homestuck}}'' is a sweet, caring, practical girl who also happens to really love wearing fake moustaches in the style of famous detectives from novels.
* In ''Webcomic/BlackAdventures'', Black and N usually fight evil in skimpy MagicalGirl costumes. Burgh and Elesa crossdress for fun (and to [[FanService titillate the fans]], apparently). The writer seems to have [[AuthorAppeal a thing for crossdressing]].
* In ''Webcomic/GirlGenius'''s "Cinderella" side-story, the three Jaegermonster men get cast as the ugly stepsisters. [[http://www.girlgeniusonline.com/comic.php?date=20081124 Maxim (in purple) really seems to enjoy the role]].
--->'''Oggie:''' ([[FunetikAksent Hyu iz]] supposed to be an ''ogly'' stepsister. Whyfor ''hyu'' gots de ''[[PimpedOutDress pretty dress]]''?)
--->'''Maxim:''' (Hyu gots to know how to ''sveet-tok'' de ''costumers'', dollink!)
* The very CampGay Dillon [=O'Brien=], when introduced in ''Webcomic/MenageA3'', 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, ''Webcomic/StickyDillyBuns'', the pattern continued, as he mostly dragged up for stage parts or as a practical disguise. When he talked [[TheIngenue the naive Ruby]] in that same comic into disguising herself as a man for one evening, that's certainly not sexual in her eyes.
[[/folder]]

[[folder:Web Original]]
* In webnovel/manga ''Cherry Girls'', everyone (probably except [[DraggedIntoDrag 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, [[EvenTheGirlsWantHer and some of them really likes him for that]].
* Leslie Audette of ''FlakyPastry'', 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...[[AnythingThatMoves would care either way]].
* In the ''{{Paradise}}'' setting, humans are randomly, permanently transformed into {{Funny Animal}}s (and occasionally [[GenderBender gender-changed]]) by causes unknown. A WeirdnessCensor renders these changes InvisibleToNormals, who continue to see the Changed as their original human selves (and genders). Any gender-Changed invariably ends up a WholesomeCrossdresser, since he or she cannot dress as the gender he or she ''really'' is or it will look strange to those not [[BrokenMasquerade 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 WhateleyUniverse, 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.
* Examples from ''Website/ThatGuyWithTheGlasses'':
** [[WebVideo/TheSpoonyExperiment Spoony]] as Spoonette and The Gate Cleaner's Wife, [[WebVideo/AtopTheFourthWall Linkara]] as 80s Chick, WebVideo/{{Benzaie}} as Veronique and WebVideo/TheNostalgiaCritic 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 RaisedAsTheOppositeGender for a bit, giving him a few issues.
** [[YouCanPlayThis JewWario]] has actually crossdressed in public on several occasions (most notably at showings of RockyHorrorPictureShow).
** Benzaie has made crossdressing a running joke on his show for sketches about his more girly interests.
** Tacoma from WebVideo/DemoReel played Oprah for a parody, and dressed as Belle from Disney/BeautyAndTheBeast to make Rebecca happy. He didn't mind either costume.
* Par for the course in any story on Website/{{Literotica}} that's in the Transsexuals/Crossdressers section and doesn't contain either [[GenderBender magic]] or {{bondage|IsBad}}.
* Possibly the most adorable example ever, ''[[http://monotremata.tumblr.com/post/47790662772/the-long-awaited-prince-and-the-princess-my The Prince and the Princess]]'' is about [[ExactlyWhatItSaysOnTheTin a young prince named Edmund who wants to be a princess.]]
* While Ashly Burch, from ''HeyAshWhatchaPlayin'', is pretty far from "wholesome", she does rock some mean costumes of male characters in many early episodes.
[[/folder]]

[[folder:Western Animation]]
* ''WesternAnimation/LooneyTunes'': BugsBunny, when he's trying to trick someone. Most notably done in ''WesternAnimation/WhatsOperaDoc''.
* WesternAnimation/WoodyWoodpecker has done this time to time, the most memorable instances being ''Chew-Chew Baby'', ''Drooler's Delight'' and ''The Woody Woodpecker Polka.''
* Pleakley in ''Disney/LiloAndStitch'' and ''WesternAnimation/LiloAndStitchTheSeries''.
** {{Justified|Trope}} in that having three legs pretty much rules out pants as an option.
*** And Jumba, to an extent. In the series he once dressed up as Pleakley's 'bride' and nearly married him.
* In ''WesternAnimation/RockosModernLife'' Heffer's stepbrother Peter seemed to like to wear cheerleading outfits and ballerina tutus.
** [[ITakeOffenseToThatLastOne Tutus are considered unisex nowadays]], though men usually wear them for comedic purposes.
* Timon of ''Disney/TheLionKing'' 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.
** In the POVSequel, Timon was still wearing the outfit when he reunites with his Ma and Uncle Max, and [[SugarWiki/FunnyMoments they don't comment on it until after Timon has left the scene]].
* Part of Override's bio from her toy on ''Anime/TransformersCybertron'' (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 MythologyGag referencing the fact that [[ShesAManInJapan in the original Japanese, she's already male]].
* Jerry from ''WesternAnimation/TomAndJerry'' also cross-dressed a few times to trick Tom, who apparently is less likely to be violent [[HelloNurse towards a girl mouse]].
* Examples from ''WesternAnimation/TheFairlyOddparents'':
** 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 AllJustADream in the Darkness' LotusEaterMachine.
** In the episode "Scary Godparents", Timmy's parents go out as each other for Halloween.
* Stewie in ''WesternAnimation/FamilyGuy'' 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.
* [[WesternAnimation/TinyToonAdventures Buster Bunny]], usually for the same reason as [[WesternAnimation/LooneyTunes Bugs]], to trick people.
* On ''WesternAnimation/JimmyTwoShoes'', both Jimmy and Lucius do this while being flight attendents.
** Jimmy ends up cross dressing frequently during the series, whether it's for disguise purposes, losing a bet or because he felt like it.
* Both Fred and Barney of ''WesternAnimation/TheFlintstones'' 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 ''WesternAnimation/TheJetsonsMeetTheFlintstones'' so they can gain access to a poker game with Mr. Slate without being recognized.
* AmbiguouslyGay King Julien of ''WesternAnimation/{{Madagascar}}'' and ''WesternAnimation/ThePenguinsOfMadagascar'' has worn skirts occasionally, though this may not count as he's a lemur and doesn't normally wear anything at all.
-->"Which of you is attracted to me?"
* Roger from ''WesternAnimation/AmericanDad''. He himself is ''anything'' but [[JerkAss wholesome]], but his frequent crossdressing is never portrayed negatively.
* ''WesternAnimation/TheAmazingChanAndTheChanClan'' character Stanley Chan has crossdressed on more than one occasion, twice for disguises and one for the sake of [[RuleOfFunny being hilarious]]. He pulls it off quite well, too.
* The ChristmasEpisode of ''WesternAnimation/CodenameKidsNextDoor'' opens with the [[HiveMind Delightful Children]] impersonating the Kids Next Door. The Delightful Children include one brown-skinned boy and a chubby girl, they are presumably the ones that dressed as Numbuh 5 and Numbuh 2, respectively.
** Numbuh 5 wore a tuxedo in an early episode.
* Several minor examples from ''WesternAnimation/TheSimpsons'':
** Bart once demonstrated how to walk in high heels to help Lisa prepare for a beauty pageant. He was disturbingly good at it.
** 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.
** 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 "Hey, I gotta accessorize."
* Unusually for a children's show (especially a Disney one), ''TheWeekenders'' twice implies that Carver is a cross dresser when his friends catch him in possession of girls' clothing.
* ''WesternAnimation/AllGrownUp'' has Phil dressed as his twin sister Lil. He seems to develop a crush on [[HoYay another boy]].
* WesternAnimation/SheZow is a LegacyHero 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 [[PunnyName 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 ''WesternAnimation/JohnnyBravo'' has dressed as a woman many times throughout the series course.
* The title character in ''Disney/{{Mulan}}''.
* Gene from ''WesternAnimation/BobsBurgers''. 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.
[[/folder]]

[[folder:Real Life]]
* LeslieCheung. In movies like ''FarewellMyConcubine'' and ''All's Well, Ends Well'' too
** [[http://oi44.tinypic.com/34pj14z.jpg Just.]] [[http://oi42.tinypic.com/3450wi9.jpg Look.]] [[http://oi43.tinypic.com/25ai1xi.jpg At.]] [[http://oi42.tinypic.com/2uiwz90.jpg These!]]
* Music/DavidBowie, who even in ''normal'' clothes evokes [[StupidSexyFlanders Stupid Sexy David]] and EvenTheGuysWantHim reactions, looks simply ''marvelous'' in a dress.
* Director Creator/EdWood. 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 GlamRock movement qualified.
* EddieIzzard 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 VisualKei bands, especially kote kei, [[LighterAndSofter oshare kei]], and [[ElegantGothicLolita lolita]] bands, have at least one crossdresser, often (though not always) the (lead) guitarist.
** [[http://4.bp.blogspot.com/-lhCWYGZBgmA/T9zBzpK5OsI/AAAAAAAAHdk/gIFvoWOFhlo/s640/gothic_2.jpeg Mana]] (lead guitarist of Moi dix Mois and formerly Music/MaliceMizer) has toned it down a little in recent years, but is still one of the most convincing crossdressers in J-rock. Bonus points for being the TropeMaker and TropeNamer of ElegantGothicLolita.
** [[http://25.media.tumblr.com/tumblr_lpq84dVgxy1qkn41po1_500.jpg Hizaki]] (guitarist) and [[AuthorExistenceFailure the late]] [[http://4.bp.blogspot.com/-Y2WeHW4PDzQ/T1eT94u5u3I/AAAAAAAAA0Y/DKn4pspDaJw/s1600/jasmine%2Byou%2B3.jpg Jasmine You]] (bassist) from Music/{{Versailles}}. Interestingly, Teru (guitarist) ''was'' one of these before joining Versailles (apparently he didn't like it all that much). This tends to trip up Versailles fans who decide to check out Hizaki Grace Project and discover [[http://userserve-ak.last.fm/serve/_/3241565/HIZAKI%2Bgrace%2Bproject%2Bteru08.jpg a blond Teru wearing a knee-length dress]].
** [[http://farm4.staticflickr.com/3264/3156208843_6a77d2cd41.jpg Bou]] (guitarist) of An Cafe.
** [[http://pics.livejournal.com/necrae_x/pic/0005y838 Sui]] (vocalist) and [[http://userserve-ak.last.fm/serve/_/52538133/Megaromania+2Misery.jpg Misery]] (lead guitarist) of Megaromania.
** [[http://images4.fanpop.com/image/photos/21300000/Mashiro-japanese-bands-21346664-743-1023.jpg Mashiro]] (vocalist) of [=PaRADEiS=].
** [[http://24.media.tumblr.com/tumblr_m6cwpgLys91qiq1olo1_500.jpg Asagi]] (vocalist) and [[http://download.minitokyo.net/D.304597.jpg Tsunehito]] (bassist) of D.
** [[http://2.bp.blogspot.com/_ibhVyCTXAAw/S7ySIigNTHI/AAAAAAAABpU/FEJ4Myi2sqc/s1600/kaya-chocolat.jpg Kaya]] (vocalist), formerly of Music/SchwarzStein, now [[Music/{{Kaya}} a solo artist]].
** From the [[DistaffCounterpart all-female]] band Music/ExistTrace, there's [[http://25.media.tumblr.com/tumblr_m6e7pkogQs1r5j9q9o1_500.jpg Omi]] (lead guitarist) and [[http://nd04.jxs.cz/639/755/cec1b15da6_76527259_o2.jpg Mally]] (drummer).
* 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.
** [[http://entrancia.files.wordpress.com/2010/02/tegoshiyuuko3.png Tegoshi]][[http://entrancia.files.wordpress.com/2010/03/news-calendar-2010-11-0491.jpg 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.
* [[http://en.wikipedia.org/wiki/Julian_Eltinge 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.
* Even the [[http://www.bbc.co.uk/news/world-europe-10896818 Mayor of Reykjavik]] qualifies!
* ''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 [[NippleAndDimed 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 DoubleStandard, given that Crossdressing women seems to be looked down upon far less than a crosdressing male. A crossdressing woman might get comments of ButchLesbian thrown at her, but a crossdressing man is likely to be seen as a CreepyCrossdresser.
* Barry Humphries playing his character Dame Edna Everage. Just because Edna's considered "wholesome" doesn't mean she's not a [[SmallNameBigEgo massively egotistical]], [[StepfordSmiler Stepford Smiling]] GrandeDame who makes [[TheRockyHorrorPictureShow Dr. Frank-N-Furter]] [[LargeHam look humble by comparison]].
* Artist Marcel Duchamp went through a transvestite period as "Rrose Selavy", a genteel-looking gentlewoman type who was photographed by Duchamp's friend Man Ray.
* Artist Grayson Perry personifies this trope. It's remarkable for him to be at a public appearance not dressed like a little girl.
* [[http://www.queerty.com/the-only-ones-who-had-a-problem-with-her-son-cross-dressing-on-halloween-were-other-mothers-20101104/ This preschool kid]] decided to go to a halloween party as Daphne from Scooby Doo. The only people with a problem with that were other children's mothers.
* [[http://en.wikipedia.org/wiki/Chevalier_d%27Eon Le Chevalier d'Eon]].
* Music/JustinBieber [[http://www.hollywoodlife.com/2011/09/09/justin-bieber-wears-womens-jeans-girls-selena-gomez/ revealed]] "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.
* LadyGaga. No, not just wearing pants, she actually goes full DragKing with her alter ego Jo Calderone.
* The ''[[http://www.youtube.com/watch?v=HaDJQui1a2Y 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 PlayedForLaughs moves.
** Similarly, and predating ''Men In Tutus'' by some years, the Ballets Trockadero de Monte Carlo.
* Brian Molko, the singer for the band Music/{{Placebo}}. [[http://www.documentingreality.com/forum/attachments/f185/66301d1246963190-brian-molko-brian_molko_01.jpg Easily ]] [[http://th00.deviantart.net/fs71/PRE/f/2010/305/4/e/placebo_brian_molko_189_by_mychael_helmz-d31yemd.jpg passes ]] [[http://fpexer118.com.sapo.pt/Placebo/Images/brian3.jpg as a ]] [[http://26.media.tumblr.com/tumblr_l6la9mqh1c1qc1uf1o1_400.jpg woman.]]
* Creator/JunichiSuwabe [[http://www.animenewsnetwork.com/interest/2013-08-14/fate/stay-night-voice-actor-junichi-suwabe-dresses-up-in-maid-cosplay-for-program is set to appear on a television show dressed as a]] {{Meido}}.
* Both the male-dressing-as-female and female-dressing-as-male varieties are common in the {{cosplay}} scene. The aforementioned DoubleStandard 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 [[UsefulNotes/AmericanFootball 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.
[[/folder]]

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