Follow TV Tropes

Following

History Main / WholesomeCrossdresser

Go To



* 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).

to:

* ''Manga/JoJosBizarreAdventure'':
**
Subverted in one chapter of ''Manga/JoJosBizarreAdventure''. The main character of Part 2, Joseph, ''Manga/BattleTendency'', where Joseph cross-dresses as a tequila girl for a disguise to fool the Nazis. He fails to realize that most women aren't quite as well-built as he is. HilarityEnsues.
** In a slightly more feminine example, Narciso Annasui Anasui from Part 6 ''Manga/StoneOcean'' 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, [[WhatCouldHaveBeen he was originally intended by Araki to be female upon his introduction, female]], only later being retconned to a male crossdresser. crossdresser ([[ExecutiveMeddling this is due to the editors being afraid the majority female cast of the Part would push away the target demographic]]). 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).course).
** In ''Manga/{{JoJolion}}'', it is tradition for the firstborn sons of the Higashikata family to cross-dress until they are 12. [[spoiler:This is done as a way to ward off a curse that turns all firstborn sons of the family to stone]].


** [[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!]]



to:

* In ''VideoGame/{{Catherine}}: Full Body'', [[spoiler: the character Rin is a kind male crossdresser who uses his powers to help the main character Vincent.]]

Added DiffLines:

* "Vicar in a Tutu" from Music/TheSmiths' ''Music/TheQueenIsDead''.

Added DiffLines:

* ''VisualNovel/HighschoolRomance'': Shoji, the main character, is accidentally enrolled in an all-girl school, but the principal Lea decides to give him a chance at staying provided that he tries to pass as a girl, even buying him lingerie and clothes. Shoji himself, despite some initial embarassment, gets used to it, and during the course of the story he can befriend and romance two other girls. [[spoiler: If Selene is chosen, it's revealed that Shoji took up crossdressing for his girlfriend's pleasure.]]


* 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.]] He also dances and lip-syncs to "Young Hearts Run Free". It's awesome.

to:

* One of the "edgy" things about Baz Luhrmann's modern remake of ''Theatre/RomeoAndJuliet'' ''Film/WilliamShakespearesRomeoAndJuliet'' 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.]] He also dances and lip-syncs to "Young Hearts Run Free". It's awesome.


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.

to:

The opposite of CreepyCrossdresser. May overlap with DisguisedInDrag or its DistaffCounterpart, SweetPollyOliver. (If the character wears crossdressing cross-dressing disguises more often than seems ''strictly'' necessary, this trope may apply.) Wholesome Crossdressers tend to ''enjoy'' dressing, even if only reluctantly, secretly, or subconsciously.



** Ciel 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 famous in the series, to the point of where it even has its 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.

to:

** Ciel 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 famous in the series, to the point of where it even has its 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.



* Hideri Kanzaki of ''Manga/BlendS'' is a boy who dresses like a girl. He works as a waitress at a cafe and desires to be the cutest. Unlike most examples, he's more similar to a RealLife transvestite--he does that because he likes it, yet he continues to see himself as male and appears to be heterosexual.
* The short lived ''Manga/BlueWars'', provides an odd example with the Sera brothers. Yuuri Sera has always looked and acted exactly like a lovely young girl and is consistently treated as such by "his" family and friends. "His" younger brother, our protagonist Ryousuke, would like to do the same but, by virtue of being more muscular and manly in appearance, is stuck to manly standards as heir of their father's dojo. The plot is driven by how he tries to get around this.

to:

* Hideri Kanzaki of ''Manga/BlendS'' is a boy who dresses like a girl. He works as a waitress at a cafe and desires to be the cutest. Unlike most examples, he's more similar to a RealLife transvestite--he transvestite -- he does that because he likes it, yet he continues to see himself as male and appears to be heterosexual.
* The short lived short-lived ''Manga/BlueWars'', provides an odd example with the Sera brothers. Yuuri Sera has always looked and acted exactly like a lovely young girl and is consistently treated as such by "his" family and friends. "His" younger brother, our protagonist Ryousuke, would like to do the same but, by virtue of being more muscular and manly in appearance, is stuck to manly standards as heir of their father's dojo. The plot is driven by how he tries to get around this.



* Seki from ''Manga/DokiDokiSchoolHours'' likes to dress up in womens' attire - actually hoping he will impress ''girls'' that way.

to:

* Seki from ''Manga/DokiDokiSchoolHours'' likes to dress up in womens' women's attire - actually hoping he will impress ''girls'' that way.



* Used as a one-off gag in ''Manga/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.

to:

* Used as a one-off gag in ''Manga/GameXRush'', where the middle-class Memori is portrayed as a "Cinderella" as oposed opposed to Yuuki's imagined wealth. Also, Memori dresses as a nurse to "avoid suspicion" and stay in the hospital after hours... to make sure Yuuki doesn't escae, of course.



* Kazuki in ''Manga/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.

to:

* Kazuki in ''Manga/GetBackers''. The writers, especially in the anime, will take any excuse they can to get him into womens' women's clothing. Sometimes it's a misunderstanding, sometimes it's part of his job, sometimes it's favor for a friend... and then there's the official art of him in womens' women's 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.



* Gaspar in ''LightNovel/HighSchoolDXD'' wears the school's female uniform and pulls it off so well everyone needs to be told he's a he on first meeting. It doesn't help that he acts shy and feminine, to the point of quickly developing a crush on [[ChickMagnet Issei]]. Issei tries to get him to start wearing more masculine clothing, at first because [[UnsettlingGenderReveal it creeps him out]], and [[CharacterDevelopment later]] because [[spoiler:Gaspar's crossdressing turns out to be rooted in trauma from his DarkAndTroubledPast and he wants his friend to move past that.]][[note]]The crossdressing itself is treated as a harmless symptom by itself[[/note]]

to:

* Gaspar in ''LightNovel/HighSchoolDXD'' wears the school's female uniform and pulls it off so well everyone needs to be told he's a he on first meeting. It doesn't help that he acts shy and feminine, to the point of quickly developing a crush on [[ChickMagnet Issei]]. Issei tries to get him to start wearing more masculine clothing, at first because [[UnsettlingGenderReveal it creeps him out]], and [[CharacterDevelopment later]] because [[spoiler:Gaspar's crossdressing cross-dressing turns out to be rooted in trauma from his DarkAndTroubledPast and he wants his friend to move past that.]][[note]]The crossdressing itself is treated as a harmless symptom by itself[[/note]]



* Hibiki-sensei in ''Anime/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.

to:

* Hibiki-sensei in ''Anime/IMyMeStrawberryEggs'', who crossdresses cross-dresses in order to get a job from a man-hating boss. His {{Mentor}} is also a transvestite whose failed marriage to the boss caused her man-hating.



* The titular character from ''Manga/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.

to:

* The titular character from ''Manga/KunisakiIzumoNoJijou'', who is already [[DudeLooksLikeALady attractive]] enough to be mistaken as a girl all the time, frequently crossdresses cross-dresses as a result of him invariably receiving female roles from his family's kabuki troupe, much to his chagrin. His senior in the troupe, Kagato, is another one, although unlike Izumo he actually enjoys it.



* An episode of ''Anime/MichikoToHatchin'' had Hatchin meeting a man whose job involves him being a crossdressing actor. While he wears men's clothes outside of work, his son dresses as a girl 24/7 and wants to be a female impersonator like his father when he grows up.

to:

* An episode of ''Anime/MichikoToHatchin'' had Hatchin meeting a man whose job involves him being a crossdressing cross-dressing actor. While he wears men's clothes outside of work, his son dresses as a girl 24/7 and wants to be a female impersonator like his father when he grows up.



* ''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 ''Manga/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?

to:

* ''Anime/NeonGenesisEvangelion'''s main character Shinji Ikari has crossdressed on two occasions, once wearing Asuka's spare plugsuit (complete with breast plates) breastplates) and again when he and Asuka are training to defeat Israfel they wear identical ... "jazzercise" outfits. In ''Manga/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?



* ''Manga/{{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.
* In ''Anime/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]].

to:

* ''Manga/{{Nononono}}'' is a ski-jumping manga by the author of ''Manga/ElfenLied''. The heroine Nonomiya is crossdressing cross-dressing and passing for her dead twin brother because only men are allowed in professional ski-jumping... and she wants to win Olympic gold. Played very seriously.
* In ''Anime/OhEdoRocket'' the reason for Genzo's crossdressing cross-dressing is never explained, but it might be an attempt to get people to notice him. Though his hair and makeup are very feminine from the beginning, he doesn't actually dress in women's clothes until near the end of the series after his mother has sold all his clothes and the only thing left for him to wear is a dress. The reactions to this are overwhelmingly positive, and he then goes on to play the female lead, Princess Moonbeam, in a [[ShowWithinAShow play that sums up the events of the series]].



* Miyashita Masashi from ''Manga/OniichanToIssho'' (official English title: ''Me & My Brothers''). His official reason for this is due to his profession as a romance novelist, whose demographic for his novels is women. Masashi ''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]].

to:

* Miyashita Masashi from ''Manga/OniichanToIssho'' (official English title: ''Me & My Brothers''). His official reason for this is due to his profession as a romance novelist, whose demographic for his novels is women. Masashi ''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.chagrin. Later, he admits that Sakura enjoys it when he dresses femininely, so it might not be such a bad thing after all]].



** 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.

to:

** 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' cross-dressing' is an insult to the profession.



** Tsubasa Kurenai, 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]]).

to:

** Tsubasa Kurenai, 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 cross-dressing homosexual guy who had been [[SweetOnPollyOliver fooled by her disguise]]).



** 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.

to:

** 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 cross-dressing since through magic, Ranma can be completely biologically female or male at anytime. Either way he does seem to spend a lot more time being a woman than strictly necessary, and several gags are made out of him willingly dressing up in some very effeminate clothes and seemingly enjoying it.



* 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.

to:

* While Nanami's gender in ''LightNovel/{{Sukisho}}'' is never explicitly discussed, his clothing is mostly [[AmbiguousGender ambigious ambiguous regarding gender]], and the non gender specific pronouns of Japanese are of no help either, everyone treats him like he always acts. His winter coat, pink bunny slippers, and the outfit he wears in the kitchen at home, places him firmly into crossdresser land.



* 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.

to:

* Quality Comics's Madame Fatal, the first cross-dressing superhero. "She" was really Richard Stanton, a retired actor, 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.



* 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.

to:

* George (who is either a crossdressing cross-dressing 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.



** It's implied that James' interest in crossdressing extends beyond [[DisguisedInDrag just doing it for disguise purposes]].

to:

** It's implied that James' interest in crossdressing cross-dressing extends beyond [[DisguisedInDrag just doing it for disguise purposes]].



* 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.

to:

* 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 cross-dressing and by that point was willing.



* 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 perverted things (they aren't, the fic is entirely SFW); once she calms down, she offers to correct Shinji's appearance.

to:

* In one ''Anime/NeonGenesisEvangelion'' fanfic, Shinji raids Asuka's clothes to try out crossdressing cross-dressing in an effort to gain acceptance from his father who raised a girl instead of him. Of course, Asuka throws a fit when she finds out as she thinks Shinji and Kaworu (who happened to be on-scene) are doing perverted things (they aren't, the fic is entirely SFW); once she calms down, she offers to correct Shinji's appearance.



* In ''WesternAnimation/PinocchioAndTheEmperorOfTheNight'', Scalawag and Igor use crossdressing in an attempt to save Pinocchio from his illusion.

to:

* In ''WesternAnimation/PinocchioAndTheEmperorOfTheNight'', Scalawag and Igor use crossdressing cross-dressing in an attempt to save Pinocchio from his illusion.



** Jumba cross dressed once in the series in a bridal gown in a sham marriage with Pleakley in order to please Pleakley's mom. The marriage itself was called off meaning that Jumba and Pleakley currently remain unmarried.

to:

** Jumba cross dressed cross-dressed once in the series in a bridal gown in a sham marriage with Pleakley in order to please Pleakley's mom. The marriage itself was called off meaning that Jumba and Pleakley currently remain unmarried.



* ''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]].

to:

* ''Film/ToWongFooThanksForEverythingJulieNewmar'' has Creator/JohnLeguizamo, Creator/PatrickSwayze, and ''[[WTHCastingAgency Wesley Snipes]]'' all as crossdressing cross-dressing 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]].



* In Takashi Kitano's ''Franchise/{{Zatoichi}}'', Geisha Seitaro 'Osei' Naruto is actualy a man.

to:

* In Takashi Kitano's ''Franchise/{{Zatoichi}}'', Geisha Seitaro 'Osei' Naruto is actualy actually a man.



* 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".

to:

* 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 makeup and she tenderly compliments him for looking, "beautiful, like Music/BarbraStreisand".



* ''Film/WelcomeToMarwen'': Mark, who likes women's shoes (particularly high heels) and collects them. Nicol mentions her brother also likes women's shoes, and clothing too. They aren't depicted badly as a result.

to:

* ''Film/WelcomeToMarwen'': Mark, who likes women's shoes (particularly high heels) and collects them. Nicol mentions her brother also likes women's shoes, shoes and clothing too. They aren't depicted badly as a result.



* In the ''Literature/BloodyJack'' series, the eponymous Jacky Faber's adventure begins when she disguises herself as a boy in order to open up more opportunities to escape her dangerous life as a homeless orphan on the mean streets of nineteenth century London. Her plan works. From then on throughout the series she dons male garb whenever necessity or whimsy calls for it.

to:

* In the ''Literature/BloodyJack'' series, the eponymous Jacky Faber's adventure begins when she disguises herself as a boy in order to open up more opportunities to escape her dangerous life as a homeless orphan on the mean streets of nineteenth century nineteenth-century London. Her plan works. From then on throughout the series series, she dons male garb whenever necessity or whimsy calls for it.



* In the ''Literature/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.

to:

* In the ''Literature/EvilGeniusTrilogy'' Cadel crossdresses several times as a disguise, starting in his disguise class at the Axis institute Institute and continuing whenever he needs to escape some kind of surveillance. He has a whole alternate identity for his female persona - Ariel Schaarp.



* This is of course a core theme of Creator/TerryPratchett's novel ''Discworld/MonstrousRegiment''. Apart from SweetPollyOliver (or rather Polly Perks, who chooses Oliver as her ''nom de guerre'' because of the song), there is also passing mention of a male officer named Wrigglesworth who was known for playing crosscast roles in his boys' school, and who is noncomittally described as being keen on "amateur dramatics" by the brass.
* 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]].

to:

* This is of course a core theme of Creator/TerryPratchett's novel ''Discworld/MonstrousRegiment''. Apart from SweetPollyOliver (or rather Polly Perks, who chooses Oliver as her ''nom de guerre'' because of the song), there is also passing mention of a male officer named Wrigglesworth who was known for playing crosscast cross-cast roles in his boys' school, and who is noncomittally noncommittally described as being keen on "amateur dramatics" by the brass.
* OlderThanPrint: The medieval Arab and Turkish epics were replete with crossdressing cross-dressing -- both males as females and females as males. The legendary hero al-Battal crossdresses to sneak into the Greek emperor's palace, and his son Madhbahun disguises himself as a princess to lure the wily villain Uqba into his clutches. In ''Sirat Dhat al-Himma'', the Muslim warrior queen dresses up as a priest and [[LesYay kisses the Greek princess Nura]].



* In ''WesternAnimation/TootAndPuddle'': ''Charming Opal'', Puddle dresses up as the tooth fairy, hoping he can sneak into Opal's room and leave a quarter for her in exchange for her tooth. He ends up being too late, because he and Toot fall asleep and by the time they wake up, it's morning. Turns out it doesn't matter, though; the tooth fairy came anyway.

to:

* In ''WesternAnimation/TootAndPuddle'': ''Charming Opal'', Puddle dresses up as the tooth fairy, hoping he can sneak into Opal's room and leave a quarter for her in exchange for her tooth. He ends up being too late, late because he and Toot fall asleep and by the time they wake up, it's morning. Turns out it doesn't matter, though; the tooth fairy came anyway.



* Jacob from Creator/NnediOkorafor's novel ''Lagoon'' is simply fascinated by women's fashions, the cuts, the colors, the fabrics - he thinks men's clothes are simply boring. In Nigerian society it is enough to make him suspect but he is shown as a decent guy.

to:

* Jacob from Creator/NnediOkorafor's novel ''Lagoon'' is simply fascinated by women's fashions, the cuts, the colors, the fabrics - he thinks men's clothes are simply boring. In Nigerian society society, it is enough to make him suspect but he is shown as a decent guy.



* PlayedWith in ''Literature/RiverOfTeeth''. When she learns that the gang needs a white, moustached man to run an important errand -- and their former candidate is not available -- Archie promptly throws on a very convincing disguise of a white, moustached man. Everyone's astonished at how handily she had such a disguise available and thinks that she may be crossdressing due to being a conwoman, but Archie reveals that she is actually [[AmbiguousGenderIdentity gender-fluid]] and sometimes simply feels like a man and wants to be seen accordingly.

to:

* PlayedWith in ''Literature/RiverOfTeeth''. When she learns that the gang needs a white, moustached man to run an important errand -- and their former candidate is not available -- Archie promptly throws on a very convincing disguise of a white, moustached man. Everyone's astonished at how handily she had such a disguise available and thinks that she may be crossdressing cross-dressing due to being a conwoman, but Archie reveals that she is actually [[AmbiguousGenderIdentity gender-fluid]] and sometimes simply feels like a man and wants to be seen accordingly.



** 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.

to:

** 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 cross-dressing after the episode ends, just for his own sake. Notably, both characters are not only heterosexuals, but they are also actually three of the show's most prolific flirters.



* In the Canadian Disney Show ''Series/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. In fact, the lack of believability was deliberate; he crossdressed in order to get a Section-8 "insanity" discharge from the Army. When Radar left, Klinger became clerk and dropped his cross-dressing gig, though this was written in due to the actor's discomfort with the idea that his now-mature children might be able to watch their dad crossdressing on TV each week.

to:

* In the Canadian Disney Show ''Series/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 members of the squad they suspect are up to no good. They use the opportunity to try and get into the girls 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. In fact, the lack of believability was deliberate; he crossdressed in order to get a Section-8 "insanity" discharge from the Army. When Radar left, Klinger became clerk and dropped his cross-dressing gig, though this was written in due to the actor's discomfort with the idea that his now-mature children might be able to watch their dad crossdressing cross-dressing on TV each week.



* This is a common occurence in ''Franchise/SuperSentai'' series:

to:

* This is a common occurence occurrence in ''Franchise/SuperSentai'' series:



*** In Magiranger vs. Dekaranger, he and Hikaru have to cross-dress again, much to the shock of Urara. Jasmine however, is not surprised.

to:

*** In Magiranger vs. Dekaranger, he and Hikaru have to cross-dress again, much to the shock of Urara. Jasmine Jasmine, however, is not surprised.



*** 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 ''Dårfinkar & Dönickar'', based on the book by Ulf Stark, spends a while masquerading as a boy at school.

to:

*** 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...schoolboys... 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 likable twelve-year-old heroine of the Swedish children's programme ''Dårfinkar & Dönickar'', based on the book by Ulf Stark, spends a while masquerading as a boy at school.



* ''Series/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 {{Transgender}} character.) The show portrays Marc's dressing as both healthy and acceptable, with only unlikeable characters being against it.

to:

* ''Series/CoronationStreet'', of all things, introduced Marc (aka, sometimes, "Marcia") in 2011, the show's first crossdressing cross-dressing character (though Hayley, introduced in 1998, is a recurring {{Transgender}} character.) The show portrays Marc's dressing as both healthy and acceptable, with only unlikeable characters being against it.



** Dragging up is a rite of passage, an essential skill ''expected'' of any British male comedian. It's a rare big name comic or comic actor who hasn't done this once in their career.
** Also part of ''The Lumberjack Song'' lyrics, where the Lumberjack puts on women's clothing, hangs around in bars, wears high heels, suspendies and a bra, wishing he was a girlie just like his dear papa. When the mounties recite the lines as chorus, they eventually get disgusted and leave.

to:

** Dragging up is a rite of passage, an essential skill ''expected'' of any British male comedian. It's a rare big name big-name comic or comic actor who hasn't done this once in their career.
** Also part of ''The Lumberjack Song'' lyrics, where the Lumberjack puts on women's clothing, hangs around in bars, wears high heels, suspendies suspendies, and a bra, wishing he was a girlie just like his dear papa. When the mounties recite the lines as chorus, they eventually get disgusted and leave.



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

to:

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



* The UTAU Ritsu Namine. How wholesome he is depends on how he's played, considering the fake breasts in his dress are [[TorpedoTits working missiles]].

to:

* The UTAU Ritsu Namine. How wholesome he is His wholesomeness depends on how he's played, considering the fake breasts in his dress are [[TorpedoTits working missiles]].



* In one of the most well loved of the [[Myth/NorseMythology Norse Myths]], Thor dons a full wedding gown in order to disguise himself as Freyja. ItMakesSenseInContext.

to:

* In one of the most well loved well-loved of the [[Myth/NorseMythology Norse Myths]], Thor dons a full wedding gown in order to disguise himself as Freyja. ItMakesSenseInContext.



* The Howling Banshees, an Eldar warrior Path in ''TabletopGame/{{Warhammer 40000}}'' are traditionally an [[AmazonBrigade all female]] squad. Males however are permitted to join their ranks. Since the Banshee is a female spirit in Eldar mythology, he adopts a female persona and female armor when wearing his 'Warmask'.

to:

* The Howling Banshees, an Eldar warrior Path in ''TabletopGame/{{Warhammer 40000}}'' are traditionally an [[AmazonBrigade all female]] squad. Males however Males, however, are permitted to join their ranks. Since the Banshee is a female spirit in Eldar mythology, he adopts a female persona and female armor when wearing his 'Warmask'.



** ''VideoGame/Persona2'' has Jun Kurosu, who not only has crossdressing listed as one of his ''official profile talents'', but also has a contact with Lisa demonstrating just how damn well he can crossdress.

to:

** ''VideoGame/Persona2'' has Jun Kurosu, who not only has crossdressing listed as one of his ''official profile talents'', but also has a contact with Lisa demonstrating just how damn well he can crossdress.cross-dress.



*** Another example would be [[spoiler:Teddie in his human form]], who can pull off cosplaying Literature/{{Alice|InWonderland}}. The other boys in the crossdressing pageant could count too, but the student body has [[CreepyCrossdresser rather negative opinions about it]].

to:

*** Another example would be [[spoiler:Teddie in his human form]], who can pull off cosplaying Literature/{{Alice|InWonderland}}. The other boys in the crossdressing cross-dressing pageant could count too, but the student body has [[CreepyCrossdresser rather negative opinions about it]].



** Copycat from Kanto is a girl who loves mimicing others. According to official art, this includes dressing up as them (whether they're male or female).

to:

** Copycat from Kanto is a girl who loves mimicing mimicking others. According to official art, this includes dressing up as them (whether they're male or female).



* ''VideoGame/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).

to:

* ''VideoGame/DeathSmiles II'' features Lei, who is a twelve year old twelve-year-old boy wearing an ElegantGothicLolita maid outfit. Apparently 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).



* 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.

to:

* Daphnis in ''VideoGame/TearsToTiara2'' crossdresses so he can follow [[TheOjou Elissa]] everywhere as her bodyguard. He fools everyone at first sight, sight and makes the goddess of war and barbarian princess complain about how to be ladylike.



* ''VideoGame/TheLegendOfZeldaBreathOfTheWild'' has Link crossdress in order to enter Gerudo City to petition their chief for aid against Divine Beast Vah Naboris, since voe (men) are forbidden from entering the city. Thankfully, the vai (women) who catch on to Link's true gender are either functional outcasts or [[AChildShallLeadThem Riju]], all of whom have their own reasons for letting him stay despite this knowledge.

to:

* ''VideoGame/TheLegendOfZeldaBreathOfTheWild'' has Link crossdress in order to enter Gerudo City to petition their chief for aid against Divine Beast Vah Naboris, Naboris since voe (men) are forbidden from entering the city. Thankfully, the vai (women) who catch on to Link's true gender are either functional outcasts or [[AChildShallLeadThem Riju]], all of whom have their own reasons for letting him stay despite this knowledge.



* In ''VideoGame/{{Fallout 4}}'', all clothing items have unisex designs, allowing crossdressing of the player character.
* Nanashi, the protagonist of ''VideoGame/ShinMegamiTenseiIVApocalypse'', can put on some lolita dresses that can be bought in the Ginza member's-only shop, and yes, [[VirtualPaperDoll they appear on his 3D model]]. It doesn't make him any less heroic.
* ''VideoGame/ToukenRanbu'', a game which features {{Anthropomorphic Personification}}s of Japanese swords as young men, has Midare Toushirou, who fights while wearing a dress. It's this way because the weapon he's based on has a wavy line pattern and not a straight one. His powerd-up Kiwame form ratchets up the girliness even further, with more frills and ribbons, giving the appearance of a MagicalGirl.

to:

* In ''VideoGame/{{Fallout 4}}'', all clothing items have unisex designs, allowing crossdressing cross-dressing of the player character.
* Nanashi, the protagonist of ''VideoGame/ShinMegamiTenseiIVApocalypse'', can put on some lolita dresses that can be bought in the Ginza member's-only members-only shop, and yes, [[VirtualPaperDoll they appear on his 3D model]]. It doesn't make him any less heroic.
* ''VideoGame/ToukenRanbu'', a game which features {{Anthropomorphic Personification}}s of Japanese swords as young men, has Midare Toushirou, who fights while wearing a dress. It's this way because the weapon he's based on has a wavy line pattern and not a straight one. His powerd-up powered-up Kiwame form ratchets up the girliness even further, with more frills and ribbons, giving the appearance of a MagicalGirl.



** Le Chevalier d'Eon is portrayed as gender-neutral and androgynous in this game, but is forced to disguise themself with a maid's dress on one of the story missions.

to:

** Le Chevalier d'Eon is portrayed as gender-neutral and androgynous in this game, game but is forced to disguise themself with a maid's dress on one of the story missions.



* One of the outfit options for Mario in ''VideoGame/SuperMarioOdyssey'' is a replica of Peach's wedding dress and veil, tailored to his measurements and complete with earrings and heels. Bowser thinks he looks amazing in it. Not that it matters, since he wasn't invited to the wedding. As for Luigi, he doesn't think it's weird that his brother's wearing a dress, just that he's wearing a ''wedding'' dress for fun.

to:

* One of the outfit options for Mario in ''VideoGame/SuperMarioOdyssey'' is a replica of Peach's wedding dress and veil, tailored to his measurements and complete with earrings and heels. Bowser thinks he looks amazing in it. Not that it matters, matters since he wasn't invited to the wedding. As for Luigi, he doesn't think it's weird that his brother's wearing a dress, just that he's wearing a ''wedding'' dress for fun.



* 707 in ''VisualNovel/MysticMessenger'' has a habit of crossdressing and pretending to go by a different name. It's never plot relevant, but he manages to confuse some of the other RFA members by being attractive in a dress.

to:

* 707 in ''VisualNovel/MysticMessenger'' has a habit of crossdressing cross-dressing and pretending to go by a different name. It's never plot relevant, plot-relevant, but he manages to confuse some of the other RFA members by being attractive in a dress.



* 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]].

to:

* Ryouta Kawara tends to show up in girls' outfits at various points in ''VisualNovel/HatofulBoyfriend''. It's played mostly for laughs, laughs since he's a pigeon. He's also the heroine's childhood friend, friend and considering the good ending of the "Bad Boys Love" route, he's probably her [[VictoriousChildhoodFriend canon love interest]].



** 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.

to:

** 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 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.

to:

* In ''VisualNovel/KiraKira'', Shika is forced to cross dress crossdress against his will. Interestingly enough, despite getting more male fans than the real girls in the band, people do catch on that he's a guy through things such as the shape of his hands. He's quite relieved when he's allowed to stop not just because he was tired of getting hit on/thought of as a pervert because he ''was starting to get used to it.'' He's still a wholesome crossdresser five years later, in Curtain Call.



* [[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]].

to:

* [[spoiler:Sayo Yasuda, also known as Shannon, Kanon 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 cross-dressing as a guy or a guy crossdressing cross-dressing as a girl. In the manga, however, it's implied that [[spoiler:Sayo was a biologically male child who was RaisedAsTheOppositeGender]].



* Parodied in ''Webcomic/ElGoonishShive'' when avowed pervert (and frequent GenderBender) Tedd is teased about trading school uniforms with Susan he vehemently protests that "[[http://www.egscomics.com/index.php?id=755 I don't crossdress in women's clothing!]]" Susan muses that [[ExactWords technically this is true]]. He cross dresses in men's clothing quite frequently but never wears women's clothing while male (with two [[http://www.egscomics.com/index.php?id=392 non-canon]] [[http://www.egscomics.com/sketchbook.php?id=792 exceptions]]) and always changes out of any women's clothing he has on before reverting to male.
* 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]].
* ''Webcomic/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 ''Webcomic/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).

to:

* Parodied in ''Webcomic/ElGoonishShive'' when avowed pervert (and frequent GenderBender) Tedd is teased about trading school uniforms with Susan he vehemently protests that "[[http://www.egscomics.com/index.php?id=755 I don't crossdress in women's clothing!]]" Susan muses that [[ExactWords technically this is true]]. He cross crosses dresses in men's clothing quite frequently but never wears women's clothing while male (with two [[http://www.egscomics.com/index.php?id=392 non-canon]] [[http://www.egscomics.com/sketchbook.php?id=792 exceptions]]) and always changes out of any women's clothing he has on before reverting to male.
* Dana and other Elle-Boys in the ''Webcomic/JetDream'' RemixComic always dress as females, 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]].
* ''Webcomic/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 to Natani's relationship with Keith.
* In ''Webcomic/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 Fusselton, on the other hand hand, wears a woman's outfit as a form of psychological warfare (and unlike the other examples is straight).



* In the ''Webcomic/{{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]]?"

to:

* In the ''Webcomic/{{Insecticomics}}'', the Insecticons are fond of donning Barbie dresses, dresses and actually look quite good in them. It's hilarious. "[[DoesThisMakeMeLookFat Does this dress make me look fat]], [[VerbalTic fat]]?"



* [[Literature/AnneOfGreenGables Green Gable]] from ''Webcomic/{{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.

to:

* [[Literature/AnneOfGreenGables Green Gable]] from ''Webcomic/{{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, 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.



-->'''Cassandra Belmont:''' He [[http://www.cvrpg.com/archive/2012/08/28 makes]] a better looking woman than I do.

to:

-->'''Cassandra Belmont:''' He [[http://www.cvrpg.com/archive/2012/08/28 makes]] a better looking better-looking woman than I do.



* 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]].

to:

* 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]].cross-dressing]].



* In ''Webcomic/ButImACatPerson'', Bianca is a bisexual woman who crossdresses.

to:

* In ''Webcomic/ButImACatPerson'', Bianca is a bisexual woman who crossdresses.cross-dresses.



** 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. A nice moment in ''Film/TheMonsterSquad'' review has Tamara wanting her crossdressing as a boy acknowledged, and he dismisses it because he's crossdressed for fun so much that it's not a big deal.
** Creator/JewWario has actually crossdressed in public on several occasions (most notably at showings of ''Film/TheRockyHorrorPictureShow'').
** 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.

to:

** 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. A nice moment in ''Film/TheMonsterSquad'' review has Tamara wanting her crossdressing cross-dressing as a boy acknowledged, and he dismisses it because he's crossdressed cross-dressed for fun so much that it's not a big deal.
** Creator/JewWario has actually crossdressed cross-dressed in public on several occasions (most notably at showings of ''Film/TheRockyHorrorPictureShow'').
** Benzaie has made crossdressing cross-dressing a running joke on his show for sketches about his more girly interests.
** Tacoma from WebVideo/DemoReel played Oprah for a parody, parody and dressed as Belle from Disney/BeautyAndTheBeast to make Rebecca happy. He didn't mind either costume.



* WesternAnimation/SheZow is a LegacyHero superheroine whose powers and costume are granted to whoever wears her ring. Originally meant for women in the family line, the latest person to wear the ring is [[PunnyName Guy Hamdon]], a pre-teenage boy who inadvertently got stuck with it. As a result, he wears [=SheZow=]'s female-intended costume as he fights crime. Guy doesn't take it well at first, but quickly becomes indifferent to it.

to:

* WesternAnimation/SheZow is a LegacyHero superheroine whose powers and costume are granted to whoever wears her ring. Originally meant for women in the family line, the latest person to wear the ring is [[PunnyName Guy Hamdon]], a pre-teenage boy who inadvertently got stuck with it. As a result, he wears [=SheZow=]'s female-intended costume as he fights crime. Guy doesn't take it well at first, first but quickly becomes indifferent to it.



** And Jumba, to an extent. In the series he once dressed up as Pleakley's 'bride' and nearly married him.

to:

** And Jumba, to an extent. In the series series, he once dressed up as Pleakley's 'bride' and nearly married him.



* 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.

to:

* 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 debatable as to whether this counts.



* 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 escape a witch-hunting mob and ends up entering a beauty pageant during the Griffins' stay in Texas, he also dressed up in another episode and pretended to be Brian's girlfriend to spark jealousy on another girl. Men at the restaurant recognized his female persona, so he's obviously used it at least once before.
* On ''WesternAnimation/JimmyTwoShoes'', both Jimmy and Lucius do this while being flight attendents.
** Jimmy ends up crossdressing frequently during the series, whether it's for disguise purposes, losing a bet or because he felt like it.

to:

* Stewie in ''WesternAnimation/FamilyGuy'' has taken to this lately. While the most prominent example is Seaon Season 5's "Boys Do Cry", in which he dresses as a girl to escape a witch-hunting mob and ends up entering a beauty pageant during the Griffins' stay in Texas, he also dressed up in another episode and pretended to be Brian's girlfriend to spark jealousy on another girl. Men at the restaurant recognized his female persona, so he's obviously used it at least once before.
* On ''WesternAnimation/JimmyTwoShoes'', both Jimmy and Lucius do this while being flight attendents.
attendants.
** Jimmy ends up crossdressing cross-dressing frequently during the series, whether it's for disguise purposes, losing a bet or because he felt like it.



* Roger from ''WesternAnimation/AmericanDad''. He himself is ''anything'' but [[JerkAss wholesome]], but his frequent crossdressing is never portrayed negatively.

to:

* Roger from ''WesternAnimation/AmericanDad''. He himself is ''anything'' but [[JerkAss wholesome]], but his frequent crossdressing cross-dressing is never portrayed negatively.



* 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.

to:

* 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 real-life examples of this trope.



** [[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.

to:

** [[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, years but is still one of the most convincing crossdressers in J-rock. Bonus points for being the TropeMaker and TropeNamer of ElegantGothicLolita.



* 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.

to:

* Danny Bonaduce was seduced by a cross-dresser, 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.



* It's not well known, but contrary to UsefulNotes/JesseJames' reputation as a [[TheGunslinger badass cowboy]] {{outlaw}}, one of his early schemes involved crossdressing as prostitutes to waylay Union soldiers so he and his fellow proslavery confederate guerillas could shank them. As noted by Creator/SamuelFuller:

to:

* It's not well known, but contrary to UsefulNotes/JesseJames' reputation as a [[TheGunslinger badass cowboy]] {{outlaw}}, one of his early schemes involved crossdressing cross-dressing as prostitutes to waylay Union soldiers so he and his fellow proslavery confederate guerillas could shank them. As noted by Creator/SamuelFuller:



** 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.
*** It is a DoubleStandard that got reversed over the course of time though: For the greater part of history, a man dressing like a woman would have been ridiculed and maybe considered as crazy, but they were left largely alone. A woman dressing like a man however was considered a criminal and got punished.

to:

** This is actually a DoubleStandard, given that Crossdressing women seems to be looked down upon far less than a crosdressing cross-dressing male. A crossdressing cross-dressing woman might get comments of ButchLesbian thrown at her, but a crossdressing cross-dressing man is likely to be seen as a CreepyCrossdresser.
*** It is a DoubleStandard that got reversed over the course of time though: For the greater part of history, a man dressing like as a woman would have been ridiculed and maybe may be considered as crazy, but they were left largely alone. A woman dressing like a man however man, however, was considered a criminal and got punished.



* [[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.

to:

* [[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 Halloween party as Daphne from Scooby Doo. The only people with a problem with that were other children's mothers.



* The ''[[https://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.

to:

* The ''[[https://www.youtube.com/watch?v=HaDJQui1a2Y Men in Tutus]]'' stage production, emphasizing the ballet maneuvers that full grown full-grown men are put through over the titular tutus and tights they're put ''in''. Yes, including the PlayedForLaughs moves.



* 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.

to:

* 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 cross-dressing 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/NationalFootballLeague 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").

to:

* The Hogettes are a group of male [[UsefulNotes/NationalFootballLeague 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 1980s and early 1990's 1990s who could dominate the line of scrimmage and pave the way for big runs (in other words, they "hogged the road").



* Paul Grappe was a French soldier of World War One who deserted in 1915 and decided to disguise as a woman to be harder to find, helped by his wife. He still lived with his wife (initially as two female roomates, then as an official "lesbian" couple after the end of the war). In 1925, he stopped crossdressing thanks to all French deserters being amnested and took back his male identity. After a decade of crossdressing, he was so accustomed of being a woman that he suffered from an identity crisis and gradually became violent and alcoholic. He eventually got shot by his wife during an argument in 1928 (she got acquitted during the trial).

to:

* Paul Grappe was a French soldier of World War One who deserted in 1915 and decided to disguise as a woman to be harder to find, helped by his wife. He still lived with his wife (initially as two female roomates, roommates, then as an official "lesbian" couple after the end of the war). In 1925, he stopped crossdressing thanks to all French deserters being amnested amnestied and took back his male identity. After a decade of crossdressing, cross-dressing, he was so accustomed of to being a woman that he suffered from an identity crisis and gradually became violent and alcoholic. He eventually got shot by his wife during an argument in 1928 (she got was acquitted during the trial).


* Moccat Mente Blue from ''Webcomic/TempleVaTi'', who is first seen delicately applying lipstick in a dress and heels while larger more masculine men of his species jab at each other with their horns. Also beaufea males, another alien species, seem to be this by default.


%% Previous thread: https://tvtropes.org/pmwiki/posts.php?discussion=1305206904000912700



[[folder:Theater]]

to:

[[folder:Theater]][[folder:Theatre]]



[[folder:Web Comics]]

to:

[[folder:Web Comics]][[folder:Webcomics]]


** The transvestite hookers on the show, despite their occupation, are another example of this trope. They're some of the most consistently kind and cheerful characters around. How wholesome are they? One of them is even voiced by ''Jack [=McBrayer=]'' (best known for playing [[Characters/ThirtyRock Kenneth Parcell]]), playing very much to type.

to:

** The transvestite hookers on the show, from "Sheesh! Cab, Bob?", despite their occupation, are another example of this trope. They're some of the most consistently kind and cheerful characters around. How wholesome are they? One of them is even voiced by ''Jack [=McBrayer=]'' (best known for playing [[Characters/ThirtyRock Kenneth Parcell]]), playing very much to type.


* And then there's [[Comicbook/{{Empowered}} the Goddamn Maidman!]]

to:

* And then there's [[Comicbook/{{Empowered}} the Goddamn Maidman!]]Maidman!]] A burly, hulking, Franchise/Batman style BadassNormal hero who also dresses up as a French maid. Complete with panties and fishnet stockings. Although there is a bit of humor wrung out of it (for example, the HypocriticalHumor of Maidman considering his own costuming choice normal and being an AnimalThemedSuperbeing embarrassing, or when Maidman admits that part of the reason why he's TheDreaded is due to his providing in-universe FanDisservice), for the most part, he's presented as a competent crimefighter and a genuine NiceGuy. There's also no hints of him being gay, trans, a DragQueen or "perverted"; he just thinks a French maid outfit makes a neat costume for crime fighting.


* WesternAnimation/SheZow is a LegacyHero superheroine whose powers and costume are granted to whoever wears her ring. Originally meant for women in the family line, the latest person to wears the ring is [[PunnyName Guy Hamdon]], a pre-teenage boy who inadvertently got stuck with it. As a result, he wears [=SheZow=]'s female-intended costume as he fights crime. Guy doesn't take it well at first, but quickly becomes indifferent to it.

to:

* WesternAnimation/SheZow is a LegacyHero superheroine whose powers and costume are granted to whoever wears her ring. Originally meant for women in the family line, the latest person to wears wear the ring is [[PunnyName Guy Hamdon]], a pre-teenage boy who inadvertently got stuck with it. As a result, he wears [=SheZow=]'s female-intended costume as he fights crime. Guy doesn't take it well at first, but quickly becomes indifferent to it.


* 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.

to:

* WesternAnimation/SheZow is a LegacyHero superheroine whose powers-enhanced powers and costume are granted to whoever wears her ring. Originally meant for females women in the family line, the latest member in the family line who person to wears the ring is [[PunnyName Guy Hamdon]], a pre-teenage boy.boy who inadvertently got stuck with it. As a result, he wears [=SheZow=]'s female-intended costume as he fights crime. Guy seems to be completely doesn't take it well at first, but quickly becomes indifferent to this, although he didn't take it too well at first.it.

Added DiffLines:

* Subaru Shiratori of ''Manga/NanashiNoAsterism'' is a boy who periodically cross-dresses. He typically borrows his twin sister's clothes to do so.


* 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.

to:

* 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
]] He also dances and lip-syncs to "Young Hearts Run Free". It's awesome.


Added DiffLines:

* ''{{Film/Dragonslayer}}'': [[spoiler: Valerian]] turns out to be one. This was begun by her parents to spare her from the lottery of virgin girls being sacrificed.

Showing 15 edit(s) of 442

Top

How well does it match the trope?

Example of:

/

Media sources:

/

Report