History Main / WholesomeCrossdresser

** You can wear any clothing or accessory items, even those that are obviously intended for the opposite sex. This extends in subsequent games to even unlocking the ability to have girl's hairstyles or shoes on a boy or vice versa. The only thing you can't do is change the face style or actually use the opposite sex clothes model (that is, putting a dress on a boy character will make it still look like a shirt, and putting a shirt on a girl will still look like a dress)- though, this last restriction is removed in the [=3DS=] version, which has skirts, pants, and dresses as separate kinds of items. While it does specifically classify clothes as masculine, feminine, or unisex, it doesn't stop you from buying them or trying them on in the store- the Able sisters comment on it but are okay with it. Male characters will even do a GirlyRun if they're wearing a skirt or dress.
** Blanca, the cat with the blank face, is evidently a male, even though "Blanca" is the feminine form, the gibber-clip is the highest-pitched one used for females, and the outfit is the female skirt. She has no name in Japan, and internationally she's been changed into a girl.
** Gracie the giraffe fashion designer, who wears fishnet-patterned, high-heeled boots, [[ShesAManInJapan is a guy in the Japanese versions]]. Saharah, the camel who sells wallpaper and carpets, is as well, though she only wears a vest and her only feminine feature is long eyelashes, so she doesn't count as this.

** ''Literature/FateZero'': Saber dresses in a business suit and [[{{Bifauxen}} looks very good in it]] and continues to crossdress in the {{Sequel}}.

* ''VisualNovel/SteinsGate'': [[http://k45.kn3.net/taringa/3/7/2/3/0/7/6/daay09/E34.jpg?8052 Ruka]] Urushibara has the personality of a polite, well-groomed and justified kind of beautiful girl. He doesn't push his opinions much upon others, but when he does he's quite bashful and blushes quite a bit. Because he's quite serious by nature, he simply believes what others say. He's a very shy person, and often turns down Mayuri's requests to cosplay.
** When they later manage to [[GenderBender turn him into a real girl]], the player as well as the main character are at first led to believe they failed, since she looks and acts exactly the same as before.

* Kate/Bob in ''Series/{{Blackadder}} II'' and ''Goes Forth'' is a SweetPollyOliver, but admits she "actually prefer[s] wearing boys' clothes" (to the confusion of Lord Flashheart, who's always more comfy in a dress). She's also the most wholesome character in the entire series, bordering on IncorruptiblePurePureness. Flashheart himself could count as an example, too. He’s not exactly ''wholesome, per se'', but he is still RatedMForManly despite his cross-dressing.

* The cheer team crossdresses as part of their performance at the sports festival in ''Manga/KaguyaSamaLoveIsWar''. Ishigami (who had joined in the hopes that it would make him happier and more social), ends up borrowing Kaguya's uniform for the event, and the scene where she has him try it on to see if it fits is the first real moment of what would become an incredibly wholesome [[LikeBrotherAndSister sibling-like bond between the two]].

* In season 2 of ''WesternAnimation/InfinityTrain'', Jesse and Alan Dracula [[PuppeteerParasite (or at least the guy in his mouth)]] put on dresses for a fashion show themed car. It's probably the one of the few Western shows along with ''WesternAnimation/StevenUniverse'' that doesn't present this as embarrassing or odd (in fact a lot of the edits on here seem to do so). The only part that can be considered funny is that Jesse has to wear the dress over his regular clothes.

* ''WesternAnimation/TheMask'': The Mask uses several female forms which has hair on them and his most favourite ones is a old teacher and a cheerleader which even better he speaks in a female voice in them and he likes to show his feminine side to people.

* ''WesternAnimation/TinyToonAdventures'': [[LegacyCharacter Buster Bunny]], usually for the same reason as [[WesternAnimation/LooneyTunes Bugs]], to trick people.

* ''WesternAnimation/LooneyTunes'': WesternAnimation/BugsBunny, crossdresses regularly. Most notably done in ''WesternAnimation/WhatsOperaDoc''.

* ''WesternAnimation/LooneyTunes'': WesternAnimation/BugsBunny, when he's trying to trick someone. Most notably done in ''WesternAnimation/WhatsOperaDoc''.

* ''Series/BlanketyBlank'': Subverted by Scouse comedian Paul O'Grady in his creation of the embittered, alcoholic, chain-smoking and sexually promiscuous Lily Savage, billed as "The Blonde Bombsite". Lily's savage and acid takes on life graced British comedy TV for quite a few years: she hosted the small-money gameshow for several years.

* ''WesternAnimation/TheMask'': The Mask uses several female forms which has hair on them and his most favourite ones is a old teacher and a cheerleader which even better he speaks in a female voice in them and the reason why he does them is due to [[RuleOfFunny being funny and a troll]] and that he likes to show his feminine side to people.

* DEA Agent "Denise" Bryson on ''Series/TwinPeaks'', played by David Duchovny. (Who, as it turns out, has ''[[AttractiveBentGender really nice legs]]''.) "She" went undercover as a crossdresser for purposes of an operation, and found out she liked it better that way.

* " The Crush Girls 25th Anniversary Memorial Match" at ''NOSAWA Bom-Ba-Ye #5 Rongai One Night Stand'' saw Yoshihiro Takayama and Wrestling/MinoruSuzuki dressed as Wrestling/LionessAsuka and Chigusa Nagayo against Kikutaro and Yoshihiro Sakai dressed as Dump Matsumoto and Bull Nakano.

Often overlaps with DragQueen (a campy, hyper-feminine form of expression with heavy ties to gay/bi male culture), but usually doesn't with being UsefulNotes/{{Transgender}} (an intricate subject that is more connected with inward identity than outward appearance).

** Aoi Hyoudou.

* Ayumu Mikoshiba from ''Manga/OtasukeMikoMikoChan'' is one, however reluctantly. A character introduced later, though, has no such qualms about cross-dressing.

* Reborn of ''Manga/Reborn2004''. Then again, he's a baby, so he can get away with it.

* Kitten from ''Film/BreakfastOnPluto'' basically personifies [[TheCutie "cute"]].

* Michael Jeter in ''Film/TheFisherKing'' could be the TropeCodifier.

* This was also how Creator/EdWood portrayed [[AuthorAvatar a thinly-disguised version of himself]] in ''Film/GlenOrGlenda''.

* ''Film/JustOneOfTheGuys'': Terry Griffith.

* Roger [=DeBris=] from ''Film/TheProducers''.
-->"I'm supposed to be the Grand Duchess Anastasia, but I think I look more like the Chrysler Building."

* ''Franchise/{{Zatoichi}}'':
** ''Film/Zatoichi2003'': In Takashi Kitano's adaptation, Geisha Seitaro 'Osei' Naruto is actually a man.

* ''Literature/{{Theatrica}}'' with the character Vivian.
* ''Literature/TheTillermanFamilySeries'': A variant in the fitst book Homecoming by Cynthia Voigt. Thirteen-year-old protagonist Dicey pretends to be a boy when on the run with her younger siblings, because she thinks she'll get hassled less as a boy. Since she has short hair and androgynous-looking clothing, she already gets mistaken for a boy pretty regularly so she just leans into it.

* Natsume, from ''Literature/TokyoRavens'' dresses as a boy in public.

* Pulaski, the cross-dressing killing machine in ''Literature/UndeadOnArrival'', is one of the more heroic characters in the novel. He's the most fabulous by a large margin.

* Clarence from ''Series/BostonLegal'' crossdressed as both an alter ego, Clarice, and ''Oprah''.

* Drew Carey's brother on ''Series/TheDrewCareyShow'', before marrying Mimi.

* ''Series/{{Glee}}'': Wade "Unique" Adams; ShrinkingViolet as a boy, SassyBlackWoman as a girl.

* British soap ''Series/{{Hollyoaks}}'' features Kris, a bisexual cross-dressing man.

* DEA Agent "Denise" Bryson on ''Series/TwinPeaks'', played by David Duchovny. (Who, as it turns out, has ''[[AttractiveBentGender really nice legs]]''.) Also a rare case of a heterosexual crossdresser on network TV.

* In a BBC modern-dress production of ''Theatre/TheTamingOfTheShrew'', Petruchio was a rare Western media example of a heterosexual crossdresser.

* Pretty much everyone in Music/{{Queen}}, in the video for "I Want to Break Free". Nice legs, Roger Taylor.

* Music/GreenDay's "King for a Day" (Princess by dawn!).
-->"''Who put the drag in drag queen?\\
Don't knock it until you've tried it''"

* The protagonist of Music/{{Placebo}}'s song "Nancy Boy".
* "Rosie" by Joan Armatrading.
* [[Music/FlorenceAndTheMachine Florence Welch]] wears a suit both in the 2008 video for "Dog Days Are Over", and in the "Sweet Nothing" video.
* "Vicar in a Tutu" from Music/TheSmiths' ''Music/TheQueenIsDead''.

* ''Literature/TheBible'': Deuteronomy 22:5. Exact meaning is debatable, though it is sometimes taken to defy this trope.
* Myth/ChineseMythology: Lan Caihe of the Eight Immortals may or may not be one. [[DependingOnTheWriter It depends on who you ask.]]

** Dionysus is often portrayed wearing women's clothes.

* ''Wrestling/DramaticDreamTeam'': Rookies Shun Miyatake and Hiroshi Fukuda were made to dress like women and to entrances of Kazuki Hirata and Magnum HIRATA.

* Shakespeare's ''Theatre/TwelfthNight'' centres around Viola disguising herself as a man and while it causes some issues in her love life she is never presented as having done anything wrong and indeed if she hadn't the happy ending likely wouldn't have occurred.

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

*** 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 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.]]

* Cissy Meldrum from ''Series/YouRangMLord''. She is a {{Bifauxnen}}, a lesbian, a crossdresser and a communist, but she is portrayed as one of the most positive characters in the series - a rare portrayal for the 90's. She gets on well with her family (except for her sister [[RichBitch Poppy]], what is {{Justified|Trope}}) and the servants, especially with the scheming butler Alf (who is a communist, too) and his daughter, Ivy the maid.

* ''VideoGame/DragaliaLost'' has Chitose, [[ReallyFondOfSleeping Mitsuhide’s]] subordinate. He loves cutes things, and his ultimate dream is to be the worlds cutest boy. That’s why Chitose likes to wear girls kimonos, and his 2D artwork even portrays him at a makeup station.

* In ''Manga/{{Beastars}}'' Legosi disguised in drags to get close to Louis.

* In ''WesternAnimation/RockosModernLife'' Heffer's stepbrother Peter seemed to like to wear cheerleading outfits and ballerina tutus.
** [[ITakeOffenseToThatLastOne Tutus are considered unisex nowadays]], though men usually wear them for comedic purposes.

** Dave wore a long frilly skirt to prove a point when [[UsefulNotes/{{Transgender}} Adam]] made him uncomfortable.

* 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 members of the squad they suspect are up to no good. They use the opportunity to try and get into the girls' locker room, are part of an all-girl sleepover and pillow fight, and are hit on by one of the supporting male characters while in disguise.
* 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 cross-dressing on TV each week.
* On ''Series/HillStreetBlues,'' Jeffry Tambor played a cross-dressing lawyer who was doing so on advice from his psychiatrist to "resolve his feminine-identity issues." (The "cure" worked, and the same lawyer later became a highly-respected judge on the series).
* DEA Agent "Denise" Bryson on ''Series/TwinPeaks'', played by David Duchovny. (Who, as it turns out, has ''[[AttractiveBentGender really nice legs]]''.) Also a rare case of a heterosexual crossdresser on network TV.
* Subverted in ''Series/LeaveItToBeaver'', where Wally is cast to play a saloon-girl in a "Summer Stock" Western; he hates the idea so much, that he ends up conning the perfect person for the role into taking it-- Eddie Haskell.
* Also subverted in Comedy Central's series ''Strip Mall,'' a male character is seduced by a supposed cross-dresser (but who is actually played by a very ''obviously'' female woman).

* In a BBC modern-dress production of ''Theatre/TheTamingOfTheShrew'', Petruchio was a rare Western media example of a heterosexual crossdresser.

* British soap ''Series/{{Hollyoaks}}'' features Kris, a bisexual cross-dressing man.
* ''Series/EastEnders'' also introduced one in the form of Les Coker, who enjoys dragging up as "Christine". Deconstructed as it's treated as a DarkSecret by his wife Pam, and when it gets out, several residents (most notably Billy Mitchell) turn against him. A major part of their story arc was Pam learning to accept Christine, which she eventually did.

* Jodie from ''Series/{{Soap}}'' dresses as a woman a few times during his "I want to be a woman" phase in season one.
* In ''Series/{{Monk}}'', it turns out that Lieutenant Disher is good at being a female impersonator. In "Mr. Monk and the Missing Granny," he is seen disguised as a homeless woman, although Monk and Sharona see through it. Also, in "Mr. Monk and the Three Julies," he is disguised as their suspect's deceased mother's body as a trap to lure him out of hiding and get a confession. Their suspect falls for the disguise.
* Wade "Unique" Adams from ''Series/{{Glee}}''; ShrinkingViolet as a boy, SassyBlackWoman as a girl.
* One of the many subplots in one of the first-season episodes of ''Series/Touch2012'' involved Norah and Shada, a pair of teenaged girls in Saudi Arabia who pose as boys just so that they can do things that women are forbidden to do, like drive.
* In ''Series/{{Portlandia}}'', Fred Armisen plays the feminine brunette Nina while Creator/CarrieBrownstein plays her boyfriend, the more masculine Lance (with a masked voice). They both do it convincingly.
* ''Series/MontyPythonsFlyingCircus'':
** All the Pythons have done this at one point, especially Creator/TerryJones, who was very good at it. After all, dragging up is a rite of passage and an essential skill ''expected'' of any British male comedian. It's a rare big-name comic or comic actor who hasn't done this once in their career.
** Also part of ''The Lumberjack Song'' lyrics, where the Lumberjack puts on women's clothing, hangs around in bars, wears high heels, suspendies, and a bra, wishing he was a girlie just like his dear papa. When the mounties recite the lines as chorus, they eventually get disgusted and leave.
* In season two of ''Series/LegendOfTheSeeker'', Zedd has to dress up as an old woman to infiltrate a castle. He seems to have a lot of fun with it, even when one of the (male) castle residents becomes infatuated with him.
-->'''Richard:''' I think you have an admirer.\\
'''Zedd:''' ''(affronted)'' Is there any reason why I shouldn't?
* James Fitzjames on ''Series/TheTerror'' wistfully considers wearing a Renaissance-style costume gown to the expedition's morale-boosting carnival and admires the effect the dress has on him while holding it against his body, but ends up settling for the more plausibly deniable choice of dressing as Britannia, the patron goddess of the British Empire- still technically crossdressing, but less overtly because Britannia herself is depicted in masculine armor over her dress.
* A frequent fixture in Comedy Central's ''Lip Sync Battles'', as both male and female performers will impersonate singers of the opposite gender. Perhaps most famously when Creator/{{Zendaya}} and Creator/TomHolland competed against each other; Zendaya did [[https://www.youtube.com/watch?v=g_K8qUK8pkQ "24 Karat Magic" by Bruno Mars]], while Tom did [[https://www.youtube.com/watch?v=jPCJIB1f7jk "Umbrella" by Rihanna]].
* ''Series/TippingTheVelvet2002'': Nan finds that she's more comfortable in men's clothing even when offstage as this saves her from harassment by men, and thus starts dressing like that most of the time. She is always portrayed positively, never changing from a sweet young woman.
* The Lolas--played by Jose Manalo, Wally Bayola and Paolo Ballesteros (who made a career of himself doing drag performances and makeup transformations on Instagram and elsewhere)--in the "Kalyeserye" segement of ''Series/EatBulaga''. Their antics were so much of a hit among audiences that some have watched the segment more for the comedy skits than the AlDub pairing itself.
* ''Series/GossipGirl2021'': Max's dad Gideon is a kind man who also likes to crossdress sometimes. No one cares.
* ''Series/GoldenGirls'': Throughout the series, Dorothy's brother Phil's cross-dressing is PlayedForLaughs up until the episode with his funeral. Sophia reveals she was actually deeply ashamed of her son's cross-dressing, and while she claimed to blame his wife for stopping it, she truthfully blamed ''herself'' for it. Rose tells her that Phil was still a decent human being, and his cross-dressing wasn't anyone's fault, and that it's perfectly all right for Sophia to have loved Phil even though he wasn't "normal."

* Quality Comics's Madame Fatal, the first cross-dressing superhero. "She" was really Richard Stanton, a retired actor who took up the persona of a [[HarmlessLadyDisguise harmless-seeming old lady]] after his daughter was kidnapped. Because no-one suspects the old lady.

* Sir Ystin, the Shining Knight from ''ComicBook/SevenSoldiers'' (and yet another Morrison creation) is a girl disguised as a boy. The New 52 version seen in ''ComicBook/DemonKnights'' is [[GenderBender a different matter]]...
* Franchise/{{Superman}}'s Pal ComicBook/JimmyOlsen has disguised himself as a woman... [[http://www.tgfa.org/comics/jimmy_olsen/jimmy_olsen.htm more than a few times]], actually. He's rather good at it.

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

* ''WesternAnimation/{{The Lion King|1994}}'': Timon ends up in a skirt in one scene ("What do you want me to do, dress in drag and do the hula?"), though since the animal characters don't normally wear anything it's debatable as to whether this counts.

* The title character in ''WesternAnimation/{{Mulan}}'' is [[SweetPollyOliver disguised as a male]] in order to replace her sickly father during a war.
* In ''WesternAnimation/PinocchioAndTheEmperorOfTheNight'', Scalawag and Igor use cross-dressing in an attempt to save Pinocchio from his illusion.
* The title character of ''WesternAnimation/{{Rango}}'' wears a dress in order to pass as a travelling actor to get some arrest-ees to let their guard down. It turns into an elaborate wagon chase scene, with him still in the dress.

* ''Series/BlanketyBlank": Subverted by Scouse comedian Paul O'Grady in his creation of the embittered, alcoholic, chain-smoking and sexually promiscuous Lily Savage, billed as "The Blonde Bombsite". Lily's savage and acid takes on life graced British comedy TV for quite a few years: she hosted the small-money gameshow for several years.

* ''Series/TheDukesOfHazzard'': The Season 6 episode "Targets: Lulu and Daisy" -- where a diamond thief and his henchmen learn that Daisy and Lulu have accidentally gotten hold of a suitcase containing a stolen necklace -- has, at Bo and Luke's behest, Rosco and Boss Hogg dress as Daisy and Lulu, respectively, hoping to lure the thieves into a trap. Plenty of bad jokes abound until the thieves kidnap (and plan to kill) the sheriff and the county administrator.

* Reality TV example: Derrick Barry on ''Series/AmericasGotTalent'' and Courtney Act on ''Series/AmericanIdol''.
* Clarence from ''Series/BostonLegal'' crossdressed as both an alter ego, Clarice, and ''Oprah''.
* Drew Carey's brother on ''Series/TheDrewCareyShow'', before marrying Mimi.

* Mr. Humphries of ''Series/AreYouBeingServed''. In one episode, he helped out by cross-dressing by pretending to be a female customer to help Mrs. Slocombe get her job back.

* Simone, the likable twelve-year-old heroine of the Swedish children's programme ''Dårfinkar & Dönickar'', based on the book by Ulf Stark, spends a while masquerading as a boy at school.
* Jack Donaghy of ''[[Series/ThirtyRock 30 Rock]]'' reveals that he exclusively wore hand me downs until he was 12. His older siblings were all girls.[[note]]"Apollo, Apollo": Season 3, Episode 16[[/note]]

* Dave in ''Series/{{Degrassi}}'' wore a long frilly skirt to prove a point when [[UsefulNotes/{{Transgender}} Adam]] made him uncomfortable.
* ''Series/CoronationStreet'', of all things, introduced Marc (aka, sometimes, "Marcia") in 2011, the show's first cross-dressing character (though Hayley, introduced in 1998, is a recurring UsefulNotes/{{Transgender}} character.) The show portrays Marc's dressing as both healthy and acceptable, with only unlikeable characters being against it.

* The original premise of 80s sitcom ''Series/BosomBuddies'' was DisguisedInDrag, but the boys carry on with the charade over the course of the series longer than seems strictly necessary.

* Kate/Bob in ''Series/{{Blackadder}} II'' and ''Goes Forth'' is a SweetPollyOliver, but admits she "actually prefer[s] wearing boys' clothes" (to the confusion of Lord Flashheart, who's always more comfy in a dress). She's also the most wholesome character in the entire series, bordering on IncorruptiblePurePureness. Flashheart himself could count as an example, too. He’s not exactly ''wholesome, per se'', but he is still RatedMForManly despite his cross-dressing.

* ''Series/{{Accused}}'': Simon, in his guise as Tracie. This even gets him acquitted, as he goes into court dressed as Tracie and successfully shows how ridiculous the idea of committing a crime in that outfit would be.

* In the pilot of ''Series/DrakeAndJosh'', it's revealed that Josh dresses up as a woman in order to write an advice column for the school newspaper. Of the two brothers, Josh is easily the nicer and kinder one.

* ''Series/ColdCase'': In "[[Recap/ColdCaseS2E22BestFriends Best Friends]]" {{butch lesbian}} Billie likes to dress in a fancy men's suit whenever she can, to reactions varying from surprise to horror. She's a nice young woman (though she puts on a tough exterior, which is not too surprising given this) who's actually been arrested for this in the past.

* Danny the Street, in Creator/GrantMorrison's (sensing a theme here?) ''ComicBook/DoomPatrol'', is a transvestite [[Main/GeniusLoci sentient street.]]
* And then there's [[ComicBook/{{Empowered}} the Goddamn 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.
* ''ComicBook/{{Fence}}'' has Bobbi who likes dressing up in girl's clothing including hair decorations.

* George (who is either a 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.

* Subverted by Scouse comedian Paul O'Grady in his creation of the embittered, alcoholic, chain-smoking and sexually promiscuous Lily Savage, billed as "The Blonde Bombsite". Lily's savage and acid takes on life graced British comedy TV for quite a few years: she hosted the small-money gameshow ''Blankety-Blank" for several years.

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

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

* Roger [=DeBris=] from ''Film/TheProducers''.
-->"I'm supposed to be the Grand Duchess Anastasia, but I think I look more like the Chrysler Building."
* One of the "edgy" things about Baz Luhrmann's modern remake of ''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.
%%* Vilma in ''Film/TakingWoodstock''.
* In ''Pret-a-Porter (Ready to Wear)'', Danny Aiello plays Major Hamilton, a buyer of sensible clothing for the Montgomery Ward catalog who is secretly a high-fashion loving transvestite. As he spends his days during Paris' fashion weeks buying up product for his company to sell to middle America his wife Louise, played by Teri Garr, combs the boutiques of the Champs-Elysees, searching for lovely things in XL for him. Near the end of the film they spend a quiet dinner together, both in couture gowns and makeup and she tenderly compliments him on looking "beautiful, like Music/BarbraStreisand".

%%%* Saga in ''Mitt liv som hund'' (My Life as a Dog).

* ''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]].
* Disney's ''Film/SwissFamilyRobinson'' had Roberta, who was disguised as a cabin boy by her father to protect her from the pirates.
* In ''Film/KinkyBoots'' main character Lola may be a performer who can dish out some truly mean words when she needs to, but when faced with ignorant and homophobic comments actively spreads understanding. 'Ask any woman what she likes most in a man: Compassion, Tenderness, Sensitivity. Traditionally female virtues. Perhaps what women truly want is a man that is fundamentally a woman.'
* Maurice and his fellow Drag Queens in ''Film/LastVegas'' initially come off as a joke about accidentally hitting on creepy crossdressers, but Sam quickly befriends them and Maurice later shows up at the party in normal business attire with his wife.
* Several in ''Film/RacingDaylight'', which takes place half during UsefulNotes/TheAmericanCivilWar and half in the modern world. Back in time, Rev. Potts (played by John Seidman) is married to Henrietta (actress Denny Dillon) who "we all knew was a man". In modern times, Seidman plays Busy-Body, who is either a cross-dressing gay man or a pre-op transgender woman. Dillon plays the Gossip, who wears overalls and fixes trucks and objects to being called a woman. Another male character paints his toenails in a whimsical moment, while a friend chortles "Nobody's telling [=RuPaul=] to take off HIS dress."
* In ''Film/HussarBallad'' a young girl, Shura, dresses as a man just for a masked ball at first, but later uses that disguise to enter the army and serves as a real Hussar officer.
* ''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.
* ''{{Film/Stardust}}'': Captain Shakespeare is revealed to like dressing in women's clothing right at the same time he's shown as ''not'' really being a bloodthirsty murderer, but a good, kind man.
* ''{{Film/Sappho}}'': Sappho dresses as a man in Greece multiple times, and is presented positively overall. Characters who know about this disapprove or react with mixed feelings however.
* ''Film/JustOneOfTheGuys'': Terry Griffith.
* ''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.
* ''Film/MiracleMile'': The transvestite at the diner is treated as a normal person and free of CampGay stereotypical behavior, which is suprising in a film from 1988. She's an accepted regular at the diner and spends a good portion of her dialogue simply trying to give proper directions across town to a businessman. When Harry tells everyone about the harrowing phone call he just answered, the rest of the diners start to panic, but she calmly dismisses it as a PrankCall.

* ''LetsPlay/EmpiresSMP'' Seaosn 2: {{Exaggerated|Trope}}. 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.

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

* Kitten from ''Film/BreakfastOnPluto'' basically personifies [[TheCutie "cute"]].

* Played more than usually straight in ''Film/EdWood'': Ed is shown to be a heterosexual who happens to find women's clothing more attractive and comfortable. This is probably because he was based on an actual person.
* This was also how Creator/EdWood portrayed [[AuthorAvatar a thinly-disguised version of himself]] in ''Film/GlenOrGlenda''.

* In ''Film/DonJuanDemarco'', the title character (played by Creator/JohnnyDepp) is at one point enslaved, and sold to a lusty Sultana. To prevent the Sultan from discovering her new personal attendant is an entirely 'unaltered' male, she disguises her new toy ([[http://www.deppimpact.com/gallery/albums/caps_djd/djd386.JPG most fetchingly!]]) in a loose-fitting jeweled sari. (One could suspect that the script-writers invented this to showcase Depp's talent for female impersonation, but it's actually lifted from Lord Byron's epic poem ''Literature/DonJuan''.)

* ''{{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.
* ''Forever Young'': A major plot point involves four boys performing the Dance of the Little Swans for their performing arts college's festival in place of four girls when three of them die in a road accident and the sole survivor suffers a serious injury afterwards.
* ''{{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]].

* It would be better to list Astolfo here, given he first appeared in ''Literature/FateApocrypha''. His looking like a lady (and even playing up gender ambiguity) has been joked about even in universe! This kinda leads into an UnsettlingGenderReveal played for laughs when Jeanne ends up seeing Astolfo walk out of the shower stark naked. Bear in mind, at this point, she somehow (in spite of her True Name Discernment skill, which should have clued her in) didn't know Astolfo was a guy. HilarityEnsues, with the end result being [[https://www.youtube.com/watch?v=sVqa7smdB1o Jeanne letting out a very high-pitched scream and Astolfo laughing about it even on the following day, while Sieg expresses disbelief that Jeanne DIDN'T know.]]

* George, from the otherwise hilariously backward children's series ''Literature/TheFamousFive'' by Enid Blyton.

* ''Literature/WhateleyUniverse'':
** Numerous characters, being UsefulNotes/{{Transgender}}, dress as the opposite gender until they have the opportunity to change physical sex. Others have already done so, but choose to wear the same clothes that they always have done. Phase is a wealthy boy who looks entirely female except for the genitalia, forcing him to have custom made clothes with a masculine cut but a feminine fit except for a loose groin. Presumably many other students in Poe house, though they are not mentioned.
** Although there is one character who is not in Poe Cottage and cross-dresses. Gotterdammerung cross-dresses because he likes it and the story that focuses on him has him unsure if he should cross-dress for Halloween.

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

* It would be better to list Astolfo here, given he first appeared in ''Literature/FateApocrypha''. His looking like a lady (and even playing up gender ambiguity) has been joked about even in universe! This kinda leads into an UnsettlingGenderReveal played for laughs when Jeanne ends up seeing Astolfo walk out of the shower stark naked. Bear in mind, at this point, she somehow (in spite of her True Name Discernment skill, which should have clued her in) didn't know Astolfo was a guy. HilarityEnsues, with the end result being [[https://www.youtube.com/watch?v=sVqa7smdB1o Jeanne letting out a very high-pitched scream and Astolfo laughing about it even on the following day, while Sieg expresses disbelief that Jeanne DIDN'T know.]]

* Yozak from ''Literature/KyoKaraMaoh'' is a 'spy' who, though taller and more muscular than his fellow bishounen, loves to disguise himself as a woman. A cheerfully flirtatious woman, even. He even carries a dress around, just in case he needs it.

* Out of all the characters in ''Literature/{{Anpanman}}'', tough guy Kamameshidon is the character on the heroes side that is the most likely to crossdress. When he gets a starring episode with a female character, it's very likely that he'll end up crossdressing as her. Thanks to his rice bowl head and deep voice...he is not that good at pulling it off. His friends, Tendonman and Katsudonman, have also crossdressed, just not as often as Kamameshidon does. This possibly could all be based on a single IncrediblyLamePun, as "o'''kama'''" is Japanese for a male crossdresser.

* Yuki Ajiadou from Creator/{{CLAMP}}'s light novel series ''CLAMP School Paranormal Investigators'' is a boy who dreams of becoming a famous actress. To that end, [[spoiler:he wears the girls' school uniform]].

* A variant in [[Literature/TheTillermanFamilySeries Homecoming]] by Cynthia Voigt. Thirteen-year-old protagonist Dicey pretends to be a boy when on the run with her younger siblings, because she thinks she'll get hassled less as a boy. Since she has short hair and androgynous-looking clothing, she already gets mistaken for a boy pretty regularly so she just leans into it.

* 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.

* OlderThanPrint: The medieval Arab and Turkish epics were replete with cross-dressing -- both males as females and females as males. The legendary hero al-Battal crossdresses to sneak into the Greek emperor's palace, and his son Madhbahun disguises himself as a princess to lure the wily villain Uqba into his clutches. In ''Sirat Dhat al-Himma'', the Muslim warrior queen dresses up as a priest and [[LesYay kisses the Greek princess Nura]].

* Sally Sweet in the Literature/StephaniePlum series. He's described as not exactly attractive and nearly every other sentence out of his mouth is a ClusterFBomb, but he is depicted as a basically nice guy (even if he's the only school bus driver around who carries an Uzi under his seat).

* ''Literature/{{Plonqmas}}'': Plonq's gay roommate Giblet dresses in a feminine slutty reindeer costume in “A Plonqmas Tale -- 2019.” It's for a good cause, though -- he's a self-described "Sexy Santa's Helper" at a Christmas party to benefit needy families.
-->Giblet was dressed in what the snow leopard could only describe as a red-sequinned onesie with white faux fur lining the openings for the legs, armless sleeves, and a low cut V down the front. He complemented that with sheer fishnet stockings and black, knee-height, high-heeled boots. Across the back of the costume, split by the zipper were the words, Santa's "Helper" (Plonq chose not to wonder why the word "Helper" was in quotes). He completed the costume with thin, elbow-length black gloves, clip-on antlers, and plastic mistletoe tied tastefully above his tail with a piece of red ribbon.

* ''Literature/TheGoodLordBird'': Onion puts on a dress as a disguise early on, and gets mistaken for a girl after that by Brown, necessitating that he continue it. Finally he tries to confess what happened, but Brown stops him (apparently already knowing it) and says this doesn't matter, only the person Onion is.

* ''WesternAnimation/TootAndPuddle'': In [[{{Novelization}} 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.

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

Often overlaps with DragQueen (a campy, hyper-feminine form of expression with heavy ties to gay/bi male culture), but usually doesn’t with being UsefulNotes/{{Transgender}} (an intricate subject that is more connected with inward identity than outward appearance).

* ''Webvideo/{{Zerolenny}}'': If there’s a dress in the game he’s playing, Lenny ''will'' put it on, and then proceed to beat the whole thing with a broken sword.
-->'''Robolenny[wearing the [[VideoGame/DarkSouls3 Antiquated Set]]]:''' I'm a Pretty Princess.

--> Jonesy: Why are you always the girl?
--> Jude: It's my delicate bone structure.

* Nezumi from ''Literature/No6'' frequently has to dress as a woman in order to perform his act in plays, and makes a rather convincing woman at that.

* ''Manga/SgtFrog'': All five Keronians have crossdressed at least once, with Keroro himself as the biggest repeat offender. On the flipside, Kululu's debut episode has him turning Aki back into a 14-year-old -- whereupon she dresses up in her son Fuyuki's school uniform and sneaks off to his school. [[GenerationXerox Their resemblance is uncanny.]]

* Natsume, from ''Literature/TokyoRavens'' dresses as a boy in public.

* [[TheHero Shinobu Nanjou]] and [[BromanticFoil Kouta Asada]] in ''Literature/TsukiTsuki'' are forced to wear a maid and a Chinese dress at the sports festival. [[http://i39.tinypic.com/2ebg9qb.jpg It's very convincing.]]

* [[RidiculouslyCuteCritter Unico the Baby Unicorn]] from the ''Manga/{{Unico}}'' series is occasionally seen wearing [[https://img17.shop-pro.jp/PA01167/688/product/111100823.png?cmsp_timestamp=20161216144821 pink]] or [[https://images-na.ssl-images-amazon.com/images/I/814CxSBXz7L.jpg yellow]] eyeliner around his face. While the protagonist doesn't dress in female clothing in the actual series. Creator/OsamuTezuka would occasionally depict him wearing a [[https://i.ebayimg.com/images/g/rjIAAOSw0JpV5cBA/s-l400.jpg red bow around his horn]] [[https://www.flayrah.com/sites/default/files/u/Fred/LyricaUnicoSpecial.jpg in numerous illustrations.]] Unico actually enjoys dressing up in female makeup, and is brifely seen wearing a red ribbon around his tail during the prologue for the 1981 animated film ''Anime/TheFantasticAdventuresOfUnico'' (which was lifted from the manga) alongside using a mirror to check his physical appearance.

* ''Literature/{{Franklin}}'': In [[AnimatedAdaptation Franklin and Friends, Franklin has no problem dressing up as his favorite superhero, Dynaroo, despite Dynaroo being a female superhero.

* Fancourt forced to chaperone as the titular ''Charlie's Aunt.''

* Out of all the characters in ''Literature/{{Anpanman}}'', tough guy Kamameshidon is the character on the heroes side that is the most likely to crossdress. When he gets a starring episode with a female character, it's very likely that he'll end up crossdressing as her. Thanks to his rice bowl head and deep voice...he is not that good at pulling it off. His friends, Tendonman and Katsudonman, have also crossdressed, just not as often as Kamameshidon does. This possibly could all be based on a single IncrediblyLamePun, as "o'''kama'''" is Japanese for a male crossdresser.

* In ''Literature/AriaTheScarletAmmo'', this is [[spoiler:Kinji's brother]]'s method to activate Hysteria Mode (which is triggered by sexual arousal). The result is so convincing that Aria thinks [[spoiler:Kana is Kinji's ex-girlfriend]]. And it actually seems to create a SplitPersonality. You can't get more "wholesome" than that.

* Noto Kanazawa aka Noto-sama, the star of the short manga ''Manga/AdvanceKitakouBroadcastingClub'' by Creator/HidekazHimaruya. He's a cross-dressing SchoolNewspaperNewshound who's often found [[NakedPeopleAreFunny stripping other people]] with his partner-in-crime, [[LovableSexManiac Yamato]] [[{{Delinquents}} Nara]] from another Himaruya comic, ''Barjona Bombers''.
** It should be noticed that the Noto in the early ''Kitakou'' stories is virtually a completely ''different'' character. He isn't a WSC, just an OrdinaryHighSchoolStudent and a bit of a ButtMonkey, as well as being [[NiceGuy much less pushy]]. After the series added ''Pure'' to its title and Himaruya started drawing ''Barjona'', Noto was revealed to be CuteAndPsycho and snapped, starting on the path to his current incarnation. This era of the comic was taken off the website though, presumably due to OldShame.
** Koedo Chiba, a minor character in the ''Pure'' part of the series, is both this and a {{Bokukko}}. Due to having been made fun of as a child for looking like a boy, she opted to actually live her life as one.
* ''Literature/BakaAndTestSummonTheBeasts'''s Hideyoshi is one, naturally. But since he has an identical twin sister, the cast and us can let it slide. [[BaitAndSwitchComparison The fact]] [[StupidSexyFlanders that Hideyoshi's a boy]], that is.

* Makoto Mizuhara from ''Anime/ElHazardTheMagnificentWorld'', Yakumo from ''Manga/SazanEyes'' and Yellow Belmont aka Lancer from ''Genesis Climber MOSPEADA''/''Robotech Third Generation'' crossdress as a plot necessity rather than for their personal tastes. I.e.: Lancer crossdresses and poses as a female IdolSinger to act as a spy for [[LaResistance the resistance group]] he's a part of, Makoto was DisguisedInDrag posing as the missing Princess Fatora, and Yakumo crossdressed for his night job.

* ''Literature/{{Haganai}}'': As soon as [[DudeLooksLikeALady Yukimura]] joins the group, Yozora insists he wear women's clothing at all times to [[{{Troll}} "strengthen his inner manliness"]]. This lasts until [[spoiler:it's revealed, to the surprise of everyone (including him), that he actually ''is'' [[LadyLooksLikeADude a woman]]...at which point Yozora starts making her dress in ''men's'' clothing]]. Yukimura has no problem with any of this.
* Xianming Lin of ''Literature/HakataTonkotsuRamens'' is a cross-dressing assassin who is initially sent out to kill the main character, but ends up working for him instead. He initially cross-dresses as part of a disguise during operations, but eventually does so even outside work as he feels it helps him maintain a connection with his long-lost sister.

* ''Literature/HaruhiSuzumiya'': Not one to let her middle class scholarship namesake have all the fun, Haruhi has her moment when she's allegedly DisguisedInDrag in chapter 3 of ''Disappearance''.

* Rin Mitani of ''Literature/HensukiAreYouWillingToFallInLoveWithAPervertAsLongAsShesACutie'' dresses as a boy during the school day, but once it's done he wears the girls' uniform before heading to the student council. The rest of the student council is fine with it since it lets him perform his duties more efficiently and they became used to it anyway.

* ''Webcomic/HetaliaAxisPowers'':
** Poland has dressed up in girls' clothes (usually miniskirts) in a few strips, which tends to weird out his {{Heterosexual Life Partner|s}} ([[HoYay or maybe not that heterosexual]]) Lithuania.
** This is also part of Italy's backstory. Austria actually thought he was a girl until he hit puberty (it's somewhat implied that Hungary found out at some point, as she doesn't seem to be fazed by the discovery), and his first love Holy Roman Empire never found out that Italy was a male, always believing him to be a girl even when he left.
*** The child versions of Canada, Romano, and the US wore similar outfits. It's a HistoricalInJoke.
** As of ''Manga/HetaliaBloodbath2010'', we've also had Hong Kong in a maid dress, and China in a qipao.
** On the [=FtM side=] there was Hungary as a teenager, though she even managed to confuse ''[[UnsettlingGenderReveal herself]]'' with it, and so is maybe more an example of RaisedAsTheOppositeGender or possibly even being UsefulNotes/{{Transgender}}...or maybe an entirely different trope known as "Hungarian Gender Confusion" in the fandom.
* Gasper in ''Literature/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 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]]

* [[spoiler:Kei]] from ''Anime/IriaZeiramTheAnimation''.
* Ayumu from ''Literature/IsThisAZombie'', as he's drafted into a ''MagicalGirl'' army after his zombie nature absorbs most of Haruna's powers, including the ability to transform into a Masou Shoujo.

* The main cast of ''Literature/OtokoNoKoWaMeidoFukuGaOsuki'' are four brothers who help their parents' MaidCafe, and dress accordingly. The middle brothers usually crossdress only for work or other cafe-related business, while the oldest and youngest brothers crossdress all the time. In fact, the oldest brother, Nao, is so feminine that the girls at school pretty much treat him as one of their own and let him use female toilet and changing room without problem.

* ''Literature/Overlord2012'' has a pair of [[CheerfulChild adorable]] [[OurElvesAreDifferent dark elf]] twins, Aura Bella Fiora and Mare Bello Fiore. The former is a [[{{Bifauxnen}} a girl who dresses]] [[{{Tomboy}} and behaves as a guy]] while the latter is a guy dressing and behaving as a girl. A bit of a subversion on the "wholesome" part, since both are evil, but [[VillainProtagonist so are all the main characters in this series]].

* ''Literature/{{Slayers}}'' does this once a season, one episode per season (except seasons 4-5). Fans of the series refer to this as Episode 17, as each crossdressing episode is the seventeenth episode in the given season (and this came from the first season's alphabet-based IdiosyncraticEpisodeNaming—the seventeenth letter is Q, creating a "queer" implication). Ironically, not just the male cast, but often support characters introduced in the episode itself as well. Perhaps the most bizarre example is the "drag-on" sea dragon in the first season, who Gourry defeats by scratching its face and forcing the dandy dragon to retreat lest it gain any defacing scars.
* While Nanami's gender in ''Literature/{{Sukisho}}'' is never explicitly discussed, his clothing is mostly [[AmbiguousGender 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.

* A variant in [[Literature/TheTillermanFamilySeries Homecoming]] by Cynthia Voigt. Thirteen-year-old protagonist Dicey pretends to be a boy when on the run with her younger siblings, because she thinks she'll get hassled less as a boy. Since she has short hair and androgynous-looking clothing, she already gets mistaken for a boy pretty regularly so she just leans into it.