History Main / WholesomeCrossdresser

* ''Series/FellowTravelers'': Frankie is a gay drag queen, while RealLife lesbian drag king Stormé [=DeLarverie=] is a minor character and friend of his. Both are nice, sympathetic people.

* 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.
* From ''[[Manga/PlusSi +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.

** Sieglinde Sullivan [[DistaffCounterpart does it]], too. Even before [[spoiler: she has to swap clothes with Ciel as a disguise]], when she wishes to wear clothes from the "outside world" and Sebastian tells her Ciel's are the only clothes her size available, she's more than okay with it (it's her staff who won't let her). Though in Sieglinde's case, she probably simply ''doesn't care'' as long as it's something different.

** Another, sadder, example is [[spoiler: Suguru who is perfectly happy being gay man living with his partner. However, he starts to grow out his hair and crossdress as a woman once his adopted son starts to get bullied in school for having two dads.]]

* ''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]].

** Loran Cehack's female alter-ego Laura Rolla in ''Anime/TurnAGundam''. [[spoiler: It's forced onto him by Guin intentionally reporting that the Gundam pilot is a woman, and the reason why is because Guin has an unhealthy lust for him. Despite Loran being straight.]]

* Alto Saotome from ''Anime/MacrossFrontier'' used to be a Kabuki actor who specialized in female roles before he became a pilot. As a result, he retains a very feminine look even when wearing male clothing. This is {{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]]]].

* Miyashita Masashi from ''Manga/MeAndMyBrothers''. His official reason for this is due to his profession as a romance novelist, whose demographic for his novels is women. Masashi ''constantly'' crossdresses and {{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 chagrin. Later, he admits that Sakura enjoys it when he dresses femininely, so it might not be such a bad thing after all]].

* Like her VideoGame [[VideoGame/Persona4 counterpart]] [[spoiler: Naoto Shirogane]] of ''Anime/Persona4TheAnimation'' is one of these.

* ''Anime/{{Pokemon}}'':

** Later in Unova he needs to set straight some snobby b’s that bad-mouthed his Snivy from a female-only circus. Cue Ashley. Cilan was also caught in the crossfire because Iris was the actual instigator.

** In Alola when he and his classmates are taking over from a sick Joy, the guys failed to find the male uniform at first. Ash was pondering at getting away with the female uniform, but that sparked interest in the girls. With a dash of makeup and Rotom’s blond wig, we get our cutest Ashley ever.
** Many of James's disguises involve wearing dresses, even when there's absolutely no reason to (once he and Jessie posed as a bride and groom- him as the bride and her as the groom). One of James' disguises involves him wearing fake breasts for a beauty contest, which got an episode of the series banned. Jessie also used to crossdress a lot as well.
** A few canonically male Pokemon have been shown in female clothing. Some of them are embarrassed but some, like Dawn's Piplup (who frequently cheered in a pink cheerleader outfit, though he also had a male kimono), aren't phased. An Unova episode even has Pikachu DisguisedInDrag by taping a heart-shape onto his tail (the earlier-mentioned return of Ashley in Unova).

%%* [[spoiler: Misora]] from ''Manga/ShimanamiTasogare''.

* ''{{Film/Colette}}'': Missy, who habitually dresses as a man, is portrayed positively (many people then felt differently about this however). As Missy has an {{ambiguous gender identity}} though this [[SubvertedTrope might not be case]].

* ''{{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.

* ''Film/Onmyoji2001'': [[spoiler: Seimei]] lets down his hair and dresses up as the goddess Ame-no-Uzume in order to open the gate to the realm of the gods.

* In ''Literature/TheGoblinEmperor'', there is [[spoiler: Kiru]], who presumably continues to wear more practical men's clothes after the [[SweetPollyOliver attempt to deceive her potential employer about her sex]] failed and she got the job regardless.

* In ''Literature/{{Loveless}}'' Sunil, who's nonbinary and uses he/they pronouns, is fine with dressing in masculine or feminine clothes, and likes playing "gender-confused" roles in plays. He also requests to cosplay as [[Franchise/ScoobyDoo Velma Dinkley]] for Georgia's surprise for Jason [[spoiler:to try winning the latter back to Shakespeare Soc]].

* ''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.

** Kagamine Len is this in "Imitation Black" and other VisualKei styled songs by natsuP. He 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.]]

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

* ''VisualNovel/FateStayNight'': Saber aka [[spoiler: King Arthur]] and in the {{Prequel}} she dresses in a business suit that [[{{Bifauxnen}} looks]] ''[[{{Bifauxnen}} very]]'' [[{{Bifauxnen}} good on her.]]

* ''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.]]

* In ''WesternAnimation/TheAmazingWorldOfGumball'' episode "The Lady," it's revealed that Richard, unable to make any guy friends, regularly disguises himself as a woman named Samantha so he can hang out with [[Series/TheGoldenGirls a group of sassy older ladies]]. At first, Gumball and Darwin are not amused, as [[MistakenForCheating they believe Richard is cheating on their mother]] with Samantha, but once they realize the truth, they immediately try to stop Richard from breaking off his friendship with the ladies. [[spoiler: Turns out two of the other ladies are actually men too.]]

* ''WesternAnimation/{{Kaeloo}}'': Stumpy is frequently DraggedIntoDrag, but once admitted, [[spoiler: under the effects of TruthSerum]], that he does enjoy dressing up as a girl. In Season 2, he frequently argues with [[TheFashionista Pretty]] about who gets to be the "girl", to her annoyance. This has led to some... [[http://kaeloo.wikia.com/wiki/File:Stumpypoledancing.gif awkward instances]].

* ''WesternAnimation/ScoobyDoo'': Scooby and Shaggy occasionally do this, usually during the chase sequences when they're trying to hide from the monsters; either they pose as a couple on a date, skirts just make a quicker disguise, or they (usually Scooby) pretend to be a she-monster to lure out the presumably-male MonsterOfTheWeek (which always works, even though the monster is usually a human in a costume).

* ''Series/FellowTravelers'': Frankie is a gay drag queen, while RealLife lesbian drag king Stormé [=DeLarverie=] is a supporting character and friend of his. Both are nice, sympathetic people.

* 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 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.

* ''Series/FellowTravelers'': Frankie is a gay drag queen, while real lesbian drag king Stormé [=DeLarverie=] is a supporting character and friend of his. Both are nice, sympathetic people.

** Implied with Kogane Kanegae from the new student council at the end of the series. He identify as a genderqueer male but wear the female Shuchi'in uniform, and it's never made clear if he's doing it by choice or if he's forced to due to having been assigned female at birth.

%%* ''VideoGame/{{Angelique}}'': Olivie from the series of dating sims for girls. Yes, he is a possible love interest in every game he appears in.

[[folder:Let's Play]]
* ''LetsPlay/EmpiresSMP'': {{Exaggerated|Trope}} in Seaosn 2. At Gem and Katherine's Princess Tea Party, every attendee is [[DressCode required to show up in a dress]], or be kicked out and shamed across the server, [[DraggedIntoDrag regardless of their gender]]. Not only does every male server-member show up (which would be 8/13 of the main cast), but all of them are neutral, if not outright enthusiastic about showing up in a pretty dress, and a couple of them have canonically worn dresses of their own volition prior to the event.
[[/folder]]

* ''Film/ToWongFooThanksForEverythingJulieNewmar'' has Creator/JohnLeguizamo, Creator/PatrickSwayze, and ''[[WTHCastingAgency Wesley Snipes]]'' all as 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 who likes him, as it [[UnsettlingGenderReveal wouldn't be fair to him]].

* This is of course a core theme of Creator/TerryPratchett's novel ''Literature/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 cross-cast roles in his boys' school, and who is noncommittally described as being keen on "amateur dramatics" by the brass.

* All three protagonists of ''Film/TheAdventuresOfPriscillaQueenOfTheDesert'', to varying degrees. Creator/TerenceStamp plays a hard-drinking but patient trans, 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.

** 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 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.

** In a slightly more feminine example, Narciso Anasui from ''[[Manga/JojosBizarreAdventureStoneOcean Stone Ocean]]'' is a very effeminate-looking crossdresser, although the "wholesome" part is highly up for debate here. While he is one of the good guys and seems to be genuinely in love (although his courtship methods are...strange, to say the least) with the main character, Jolyne, he is also an [[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 CreepyCrossdresser, depending on who you ask. His appearance becomes ''much'' less feminine over time, with him pretty much being fully masculinized by the end of ''Stone Ocean'' (other than the women's clothes, of course).

* ''Webcomic/{{Spinnerette}}'': [[Literature/AnneOfGreenGables Green Gable]] 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.

* ''Webcomic/FlakyPastry'': Leslie Audette, who is first introduced when Marelle and Nitrine are interviewing potential roommates. The author had originally planned for the two of them to be surprised by him (i.e. "Wait, you're a ''guy?''), but then realized that Marelle wouldn't care, and Nitrine...[[AnythingThatMoves would care either way]].

* ''WesternAnimation/MadagascarEscape2Africa'': Near the beginning of the film, when the four main characters are about to leave on the plane, Maurice appears with a [[JumpingOutOfACake cake that King Julien pops out of]] wearing a combination of [[PomPomGirl cheerleader]] and [[HulaAndLuaus hula outfit]] that consists of a coconut bra, grass skirt, and grass pom-poms. Of course whether this counts or not is unknown as he normally does not wear ant clothes except for his crown. This also interestingly plays with certain [[WMG/ThePenguinsOfMadagascar Wild Mass Guessing]], to whether if Julien is [[AmbiguouslyGay gay]], [[AmbiguouslyBi bi or pan]] in addition to his [[AmbiguousGenderIdentity gender identity]], due to [[AnimalGenderBender him being a male ruler]] when lemurs are [[{{Matriarchy}} matriarchal]], leading to the audience to wonder if he is [[UsefulNotes/{{Transgender}} trans man]] or [[NonHumanNonBinary nonbinary]], who allows his fellow AnimalGenderBender subjects access to gender affirming care through a BackAlleyDoctor.

** Immplied with Kogane Kanegae from the new student council at the end of the series. He identify as a genderqueer male but wear the female Shuchi'in uniform, and it's never made clear if he's doing it by choice or if he's forced to due to having been assigned female at birth.

** Jumba cross-dressed once in a bridal gown so that Pleakley could get out of an ArrangedMarriage. Sadly, the marriage itself was called off with arrival of Gantu, who scared off the wedding chapel owner just as he was about to finish, leaving the pair currently unmarried.
* ''WesternAnimation/LooneyTunes'': WesternAnimation/BugsBunny, changes his gender presentation regularly. Most notably done in ''WesternAnimation/WhatsOperaDoc''.

* ''WesternAnimation/ScoobyDoo'': Scooby and/or Shaggy occasionally do this, usually during the chase sequences when they're trying to hide from the monsters; either they pose as a couple on a date, skirts just make a quicker disguise, or they (usually Scooby) pretend to be a she-monster to lure out the presumably-male MonsterOfTheWeek (which always works, even though the monster is usually a person in a costume).
* ''WesternAnimation/SheZow'': The titular character 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.

** Jumba cross-dressed once in a bridal gown so that Pleakley could get out of an ArrangedMarriage. Sadly, the marriage itself was called off with arrival of Gantu, who scared off the wedding chapel owner just as he was about to finish, leaving the paircurrently unmarried.

* Marco Diaz from ''WesternAnimation/StarVsTheForcesOfEvil'' crossdressed to infiltrate St. Olga's Reform School For Wayward Princesses. He not only leads a rebellion but his Princess Turdina persona becomes an IconOfRebellion and he receives monthly royalty checks for merchandise. When Miss Heinous exposed him to the other princesses (right when he was about to confess the truth himself, ironically enough), the princesses are accepting of the revelation, saying he can be a princess if wants to. Even Marco's own parents don't bat an eye when he puts on his Turdina facade in front of them. It’s gotten to the point that one of the show’s most common fan theories is that Marco is actually a [[TransAudienceInterpretation closeted]] UsefulNotes/{{Transgender}} woman.

* 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.
** Later, a dress based on Hariet the Broodal's was released, complete with stockings and heels. Again, Bowser thinks he looks amazing, while Luigi just thinks it looks familiar.