History Main / CreepyCrossDresser

* RealLife head of the Nazi ''Luftwaffe'' Herman Goering was depicted as a transvestite in a 1988 TV Movie, ''The Man Who Lived at the Ritz'', based on A.E. Hotchner's novel.

* Chapter 279 of ''Manga/AirGear'' reveals that the villainous loli Shalott who dresses in a frilly dress and wears a NiceHat is [[UnsettlingGenderReveal actually a guy]].

* [[spoiler:Rudy D'Avanzo]] from ''VideoGame/GrandTheftAutoChinatownWars''.

[[caption-width-right:350:[[JustForFun/{{Hello}} Hi...]]]]

* In ''Comicbook/AmericanFlagg'', [[spoiler:Ivor Overholt]], who makes himself into a doppelganger for the presumed-dead [[spoiler:Peg Krieger]] in order to seduce and blackmail a character who was obsessed with her. Possibly a borderline example of EasySexChange as well, though the character still had his original genitalia and still appeared as a man in public.
* In Creator/GrantMorrison's ''Comicbook/ArkhamAsylumASeriousHouseOnSeriousEarth'', the Joker was originally going to be sporting a costume with Madonna's signature cone-shaped bra and stilletto boots, simply because [[ForTheEvulz he knew it would make Batman highly uncomfortable]].

* Dark Sun Gwyndolin from ''Videogame/DarkSouls'' was a male moon god born to a family of sun gods. As the moon is associated with femininity he was raised as a daughter and wears feminine clothing which makes it looks like he has breasts. The 'creepy' part comes from the fact he lurks in a hidden tomb and has ''dozens of snakes for legs.'' His personality is otherwise fairly normal.

* Kefka is the only male character other than Cloud who is allowed to wear the crossdressing items in ''VideoGame/DissidiaFinalFantasy''. Then again, given that in the same game his official preferred weapons are ''flutes'' this might be an invocation of the RuleofFunny.

* [[spoiler:Chelsie Warner]] of ''{{WebComic/Concession}}'' is not technically a villain, but is definitely [[CreepyChild problematic]].

* In the ''WesternAnimation/JoeOrioloFelixTheCat'' episode [[Recap/JoeOrioloFelixTheCat1x08BlubberinoTheWhale "Blubberino the Whale"]], The Professor briefly disguises himself as a mermaid with a bowl of fruit just to tease the marooned and starving Felix. He quickly sheds the disguise and sics a shark after Felix.
* Ice Man, of all characters, has a go at this in the beginning of the ''WesternAnimation/MegaMan'' episode "Ice Age".

* HIM, the FlamingDevil from ''WesternAnimation/ThePowerpuffGirls'', usually dresses in a fuzzy pink skirt and thigh-high stilleto boots. His voice also tends to shift between falsetto and a deep growl depending on his mood.

A {{Crossdress|er}}ing character whose choice of attire is played for weirdness, for creepiness, for {{Squick}}, simply for shock value, or to show that he (and it's virtually [[AlwaysMale always "he"]]) is evil or deranged. While the look of the WholesomeCrossdresser tends to gloss over the dissonance between genders, this trope often calls attention to it. Often, this crossdresser exaggerates TertiarySexualCharacteristics without bothering to cover up secondary ([[FullFrontalAssault or primary]]) ones. MakeUpIsEvil is played UpToEleven. Frequently, the [[UnfortunateImplications unfortunate implication]] is that crossdressing is, in itself, creepy, but it may simply be one aspect of a character who's ''generally'' creepy.

* [[EvilTwin Rosiel]] from ''Manga/AngelSanctuary'' often [[IncrediblyLamePun skirts]] the line with his ''[[FashionVictimVillain unusual]]'' outfits. AntiVillain [[{{Bifauxnen}} Belial]] also counts.

** Charlotte Chuhlhourne is a flamboyant MagicalGirl parody. His normal attire may involve trousers, but he wears a tight tank top with plunging, frilly neckline and bared midriff, and his trousers expose the tops of his thighs on each side as well as revealing a little too much of his [[FanDisservice pelvic area]]. His hair is very long and painstakingly curled and styled and he wears long, false eyelashes. In his Resureccion form, called ''Reina de Rosas'', he transforms into a frilly, bikini-style tutu costume that is designed with the petals of a [[FlowerMotif rose]] in mind. He's extremely proud of his [[MachoCamp muscular strength]] and his costumes are designed to show off his body as much as possible.

* ''Film/AceVenturaPetDetective'': The title detective gets particularly grossed out when he learns that the "woman" he kissed earlier in the film is actually a guy who had [[DisguisedInDrag stolen the identity]] [[DeadPersonImpersonation of a missing hiker]].
-->'''Ace Ventura:''' Einhorn is Finkle... Finkle is Einhorn! EINHORN IS A MAN! (''{{beat}}'') [[OhCrap OH MY GOD!]] [[UnsettlingGenderReveal EINHORN IS A]] ''[[UnsettlingGenderReveal MAN?!]]''
** Pretty much ''everybody else'' (yes, ''even the '''dolphin''''') is just as grossed out when Ace reveals it, in fact.

* One of the "Majima Everywhere" encounters from ''VideoGame/{{Yakuza}} Kiwami'' is "Goromi-chan", AKA [[FaceOfAThug Majima]] in a pink go-go dress, fishnets, high heels, and a blonde wig. All in the name of sweet talking "Kiryu-chan" into getting in to a drag-out fight in the street when Kiryu "spurns" him.

* ''VisualNovel/PhoenixWrightAceAttorneySpiritOfJustice'' has [[spoiler:Queen Ga'ran Sigatar Khura'in, who dressed herself up in the clothes and attire that belonged to the corpse of Dhurke Sahdmadhi as part of a DeadPersonImpersonation in her effort to frame him for the murder of her HeroKiller husband Inga Karkhuul Khura'in]].

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Japanese works tend to play up a few common traits for this character type: a combination of a gaudy outfit, a NoblewomansLaugh and absolute narcissism. He also often has a crush on the BigBad, TheDragon, or in more humorous works, the ChasteHero.

** The androgynous but genuinely male Envy has traits of this which were especially played up in the English dub, where his voice is more feminine. This only applies in the 2003 anime, however, as Envy in [[Manga/FullmetalAlchemist the manga]] has no gender (or, according to [[WordofGod Word of God]], no one knows Envy's true gender – not even Envy).

** Zigzagged with the inhabitants of Kamabakka Kingdom, the original followers of Emporio Ivankov. They're certainly creepy looking, since they are ''very'' bad at crossdressing--simply throwing on cutesy female clothes and makeup on unshaven and [[{{Gonk}} hideously masculine]] bodies. But they're presented as being fundamentally decent people who don't want to hurt anyone. But then again, they're also very ''bad'' at taking "no" for an answer when it comes to guys not wanting to become "okama" like themselves. And yet at the same time, they were also instrumental in helping Sanji [[TookALevelInBadass get stronger]] during the TimeSkip.

* Fish Eye from ''Manga/SailorMoon'' has shades of this, though is clearly intended to appeal to the fetish. As the other villains disguise themselves, the HandWave is dressing as a woman is simply a ''modus operandi'' to cover the [[CastSpeciation left over type of victims - males]] - as Hawks Eye targeted older women and Tigers Eye targeted younger women. He actually dresses as a male for a specific mission (targeting gay fashion designer Yoshiki Usui), and while exclusively using ''male'' pronouns when in circus attire, will only use ''feminine'' pronouns when disguised. Ironically, his femininity seems to make him [[WomenAreWiser closer to Earth]], and he has the first HeelFaceTurn of the season.

* ''Film/TheCelluloidCloset'': One scene from ''Film/FreebieAndTheBean'' is pointed out where a depraved crossdresser is murdered in cold blood, and how audiences in the theater ''cheered'' it loudly.[[note]]After a lengthy chase, the “transvestite” villain shoots Bean, seriously injuring him, and Freebie faces him in a final showdown in a bathroom at the baseball stadium. Freebie is beaten at first, knocked on the ground by the “transvestite” who interrupts his kicks and punches for a little preening time, but eventually Freebie manages to grab a gun and empties it into the transvestite’s chest. Audiences reportedly cheered at the death scene, not just happy for the villain’s demise but cheering “the death of the fag.” Notably, the shooting was deemed too violent for network reruns of the film, who removed several of the gunshots to reduce it down to just two. - [[https://shebloggedbynight.com/2012/queer-film-blogathon-freebie-and-the-bean-1974/ Queer Blog-a-Thon]][[/note]]

* In the ''Series/NYPDBlue'' episode "Andy Appleseed" (season 11), the detectives go to the apartment of a murdered woman because they think the suspected murderer may be there. They find him in her closet, trying on her bras and panties.

* ''WesternAnimation/AdventureTime'': At the end of season six, Princess Bubblegum is usurped by the King of Ooo as ruler of the Candy Kingdom. In "Varmints", one of the first episodes of season seven, Marceline pops into Bubblegum's old bedroom to find the King wearing a wig and Bubblegum's pajamas.

* In ''VideoGame/SaintsRow2'', ''VideoGame/SaintsRowTheThird'', and ''VideoGame/SaintsRowIV'' the player can dress their character in any clothes in the game, regardless of gender. So the player can make their character a transvestite, or even UsefulNotes/{{Transgender}} through EasySexChange, if they so desire. This can go into "Creepy" territory instead of "[[WholesomeCrossdresser Wholesome]]" by having a hugely muscled man running around in a tiny dress or worse/more hilarious a string bikini and beating random passerby's to death with [[WrestlerInAllOfUs wrestling moves]] and [[GroinAttack nut punches]] when he isn't blowing their brains out or running them over in a tank. In the third game, there's also a [[GiantMook Brute]], an 8-by-4 foot mountain of muscle, dressed like a naughty schoolgirl in the dungeons of a S&M sex club. There is no context for it being there outside of the club is run by [[BigBad the Syndicate]] and it's funny.

* Kamek from the ''[[Franchise/SuperMarioBros Super Mario]]'' series dons Princess Peach's dress and a wig as a disguise in both ''VideoGame/NewSuperMarioBrosU'' and ''VideoGame/MarioAndLuigiDreamTeam''....and, in the latter, accidentally confirms that he likes wearing the dress. ''VideoGame/MarioAndLuigiPartnersInTime'' also sees him wearing a frilly, white lace apron over his usual robe.

* ''VisualNovel/DanganronpaV3KillingHarmony'' plays with this trope; Tsumugi is the Ultimate Cosplayer, which means she is revealed to be a very adept at crossplaying as well. This would fall under the WholesomeCrossdresser trope if it weren't for the circumstances in which she shows off this talent, namely that [[spoiler: she's using her talent to cosplay and crossplay as all the previous Danganronpa protagonists, revealing that she's the true ringleader of the killing game and that the previous Danganronpa characters were all fictional characters.]]

* ''Series/ArrestedDevelopment'' has a few:
** Tobias would be "wholesome" in his motivation, but the results creep out pretty much everybody:
*** After Lindsey kicks him out, several episodes have Tobias dressing as an elderly British nanny so he can stay close to his daughter.
---->'''Narrator''': It was the [[LampshadeHanging exact plot]] of ''Film/MrsDoubtfire''.

* ''Series/MrRobot'': An apparent bigwig in the Dark Army, a mysterious hacker mercenary organization, is dressed as a woman during his brief meeting with the hero. It's never commented on, and in a later scene he wears a classic men's tuxedo, possibly implying that he was deliberately using the trope to mess with the hero's head.

* ''Literature/IClaudius'' features a scene where [[TheCaligula Caligula]] (see below under real life) summons the title character and two other men out to his palace unexpectedly, scaring all three shitless because they expect to be executed, only to shock them when he prances out in full drag and does a performance for them. Also mentions the real life incidents where he dressed as Venus.

** "Machismo" was RippedFromTheHeadlines about Mataviejitas, "The Old Lady Killer". It featured a man who dressed as a woman to gain entrance into old elderly women's apartments to kill them. The actual case is a subversion. Authorities believed the killer was a man dressing as a woman; in fact, she was just a woman. It's worth pointing out that the show lampshades and (perhaps?) subverts the trope, explicitly stating that their villain is ''not'' a crossdresser: dressing as a woman is not a lifestyle for him, but a tactic.
*** It may have actually been more than a tactic. Before he became a serial killer, he was a serial rapist, and even then he wore dresses and the like, despite having no apparent reason to (he didn't use a ruse then, just blitzed the victims, who never really saw him, since he came up from behind and blindfolded them).

* A man in ''VideoGame/FableII'' is wearing a very crude attempt at a home-made woman's outfit. It turns out that he's insane and trying to feed people to his adopted family of goblin-like monsters. The game allows the player character to cross-dress, but no other characters do.
* In ''VideoGame/SaintsRow2'', ''VideoGame/SaintsRowTheThird'', and ''VideoGame/SaintsRowIV'' the player can dress their character in any clothes in the game, regardless of gender. So the player can make their character a transvestite, or even UsefulNotes/{{Transgender}} through EasySexChange, if they so desire. This can go into "Creepy" territory instead of "[[WholesomeCrossdresser Wholesome]]" by having a hugely muscled man running around in a tiny dress or worse/more hilarious a string bikini and beating random passerby's to death with [[WrestlerInAllOfUs wrestling moves]] and [[GroinAttack nut punches]] when he isn't blowing their brains out or running them over in a tank. In the third game, there's also a [[GiantMook Brute]], an 8-by-4 foot mountain of muscle, dressed like a naughty schoolgirl in the dungeons of a S&M sex club. There is no context for it being there outside of the club is run by [[BigBad the Syndicate]] and it's funny.

* [[spoiler:Thomas [=MacLaine=]]] in ''VideoGame/DeadlyPremonition'', who at that point in the story has been in such a massive TraumaCongaLine as well as [[spoiler:being the villain's ReplacementGoldfish for the woman he actually loves]] that he's gone completely off the edge of sanity.
* [[spoiler:Rudy D'Avanzo]] from ''VideoGame/GrandTheftAutoChinatownWars''.
* Though Ghirahim from ''VideoGame/TheLegendOfZeldaSkywardSword'' has a pretty effeminately flamboyant appearance, he generally doesn't seem to be outright wearing ''women's'' attire, as would be true to this trope. Still, a few elements of his appearance seem to border on it, particularly in the way his face looks like it's covered in women's makeup, e.g. heavy pink eyeliner and white lipstick.
** Yuga from ''A Link Between Worlds'' is an androgynous male antagonist who is obsessed with beauty and perfection.
* ''VideoGame/{{beatmania}} IIDX 19 Lincle''[='=]s ''Lincle Kingdom'' event features Rche, one of the bosses of the event, representing [[SevenDeadlySins Pri]][[{{Pride}} de]]. He is dressed very femininely and his gender is often (but not always!) censored in [[AllThereInTheManual supplemental material]]. His name is a play on "[[{{Satan}} Lucifer]]", and his "attack" consists of him [[JumpScare suddenly]] transforming into a goat and firing at the [[PlayerCharacter Q-pro]].
* ''VideoGame/PlantsVsZombies2ItsAboutTime'': In the Zombot Multi-Stage Masher fight, Dr Zomboss stands on a stage and changes his clothes to fit the current Jam. During the Pop Jam, he dresses up like a popstar girl with a dress and red wig. Take note that Zomboss is a midget male zombie with an [[MyBrainIsBig oversized brain]].
* [[http://megamitensei.wikia.com/wiki/Drag_Queen Undead Drag Queens]] appear as early-game enemies in ''Franchise/ShinMegamiTensei: Devil Summoner: VideoGame/SoulHackers''. You could potentially recruit them, but given that they're of the Dark affinity and you only get the ability to recruit Dark demons quite a bit later in the game, it's not worth it except for OneHundredPercentCompletion. Recruiting one (or getting one through fusion) reveals in the Compendium that they are men who somehow became zombies as a result of their devotion to cross-dressing.
* Dark Sun Gwyndolin from ''Videogame/DarkSouls'' was a male moon god born to a family of sun gods. As the moon is associated with femininity he was raised as a daughter and wears feminine clothing which makes it looks like he has breasts. The 'creepy' part comes from the fact he lurks in a hidden tomb and has ''dozens of snakes for legs.'' His personality is otherwise fairly normal.

* Kamek from the ''[[Franchise/SuperMarioBros Super Mario]]'' series dons Princess Peach's dress and a wig as a disguise in both ''VideoGame/NewSuperMarioBrosU'' and ''VideoGame/MarioAndLuigiDreamTeam''....and, in the latter, accidentally confirms that he likes wearing the dress. ''VideoGame/MarioAndLuigiPartnersInTime'' also sees him wearing a frilly, white lace apron over his usual robe.
* Monsieur Scarlet from ''VideoGame/BugFables'' wears red effeminate attire with a dress, damsel hat, and a pink umbrella, and he is also a SerialKiller who preys on unsuspecting exploration teams via luring them with [[WoundedGazelleGambit false help requests]] and then [[VampiricDraining draining their life-force to the husk]]. Ironically, he is [[TheOneGuy the only male ant]] encountered in the game.

* ''VisualNovel/DanganronpaV3KillingHarmony'' plays with this trope; Tsumugi is the Ultimate Cosplayer, which means she is revealed to be a very adept at crossplaying as well. This would fall under the WholesomeCrossdresser trope if it weren't for the circumstances in which she shows off this talent, namely that [[spoiler: she's using her talent to cosplay and crossplay as all the previous Danganronpa protagonists, revealing that she's the true ringleader of the killing game and that the previous Danganronpa characters were all fictional characters.]]

* In ‘’ VideoGame/GrandTheftAutoV'', Trevor can buy and wear dresses, which naturally invokes this reaction from passerby. One scene when you switch to him also sees him waking up from a drinking binge atop a mountain in a dress.

* ''Webcomic/LastRes0rt'''s Kurt Striaeta is not-so-ironically nicknamed "Geisha" and shown in his mugshot wearing a very feminine kimono. The surprising part is, he's actually one of the few "explicitly evil" criminals in the comic.

* Red Mage from ''Webcomic/EightBitTheater'' often wears a dress for not always apparent reasons.

* A female example in ''Webcomic/ElsannaBramStokersDracula'', where Elsa crossdresses as a Victorian gentleman. As a result, Anna (as Mina Harker's expy) does not have a good first impression of her.

* ''WebVideo/TenLittleRoosters'' episode 3 has Miles [[spoiler:running around, wearing Lindsay's [[WebAnimation/{{RWBY}} Ruby Rose]] cosplay dress, complete with make up and lipstick.]]

* In the WesternAnimation/JoeOrioloFelixTheCat episode [[Recap/JoeOrioloFelixTheCat1x08BlubberinoTheWhale "Blubberino the Whale"]], The Professor briefly disguises himself as a mermaid with a bowl of fruit just to tease the marooned and starving Felix. He quickly sheds the disguise and sics a shark after Felix.
* HIM, the FlamingDevil from ''WesternAnimation/ThePowerpuffGirls'', usually dresses in a fuzzy pink skirt and thigh-high stilleto boots. His voice also tends to shift between falsetto and a deep growl depending on his mood.
* Sakko from ''WesternAnimation/SuperRobotMonkeyTeamHyperforceGo''.
* Ice Man, of all characters, has a go at this in the beginning of the ''WesternAnimation/MegaMan'' episode "Ice Age".

* In ''WesternAnimation/FostersHomeForImaginaryFriends'', there's a creepy looking bearded homeless man who wears a dress and keeps reappearing in some episodes.
* In ''WesternAnimation/BatmanTheBraveAndTheBold'' ComicBook/TheJoker disguises himself as an Amazon to try and kill Franchise/WonderWoman.
* In ''WesternAnimation/AmericanDad'', Roger goes out in public using male ''and'' female disguises.

* In ''Manga/Brave10'', one of the [[VillainOfTheWeek villains of the week]], Ishikawa Goemon, turns out to be one. Since his whole family was targeted to be exterminated, he had to disguise himself as a girl. TokenEvilTeammate Kamanosuke has also used this to [[WoundedGazelleGambit trick people]] back when he was a bandit.
* Even ''Anime/PrettyCure'' got in on this, as [[Anime/HappinessChargePrettyCure Phantom, the Pretty Cure Hunter,]] went into battle as Cure Un-Lovely, a Cure Lovely lookalike dressed in [[RedAndBlackAndEvilAllOver red and black]], in one episode.
* In ''LightNovel/TheGardenOfSinners'', Lio Shirazumi starts dressing and styling himself like Shiki and committing murders like this. The fact that he manages to look seriously creepy in a rather silly looking skirt says a lot.
* ''Manga/FragmentsOfHorror'' story "Magami Nanakuse" is about the eponymous author, a cruel personality who has a bizarre memetic influence on people when she makes weird gestures, or tics, and she imprisons people to watch them develop tics of their own so she can write about them. She also happens to be biologically male (though it's not clear whether she's been in drag or is trans), which the protagonist insults her for after being accused of being a faker and a liar herself, arguing that Nanakuse just as bad for dressing contrary to her sex.
* ''Anime/{{Tamagotchi}}'' gives us a decidedly more innocent example. In one episode, Himespetchi's crush on Mametchi reaches the point where she crossdresses as him. While it's unsettling to everyone else, she's not being outright malicious.

* The Purple Marauder, transvestite women-hating archnemesis of the AntiHero Lusiphur, the elvish protagonist of the series ''ComicBook/PoisonElves'' (originally titled "I, Lusiphur") by late artist/writer Drew Hayes (1969-2007). The Purple Marauder (a human) is a foppish Zorro-like vigilante swordsman who terrorizes the world of Amrahly'nn with his rapier and mustache-twirling villainy but mainly with the sight of his hairy fishnet-clad legs. He dresses, as the name insinuates, all in purple from head to toe: large purple hat, purple women's dress, purple boots. His sworn mission: To convert men from the ways of lust and women.
* While he's technically more of a mercenary with a small modicum of heart and it was only the once, when ComicBook/{{Deadpool}} spent a brief time with the X-men he insisted on wearing one of their costumes. Specifically, Marvel Girl's. For unknown reasons he also retained the underwear from the costume underneath his suit even when he went back to his black-and-red tights.
* In Creator/GrantMorrison's ''Comicbook/ArkhamAsylumASeriousHouseOnSeriousEarth'', the Joker was originally going to be sporting a costume with Madonna's signature cone-shaped bra and stilletto boots, simply because [[ForTheEvulz he knew it would make Batman highly uncomfortable]].

* In ''ComicBook/LoriLovecraft: Into the Past'', MoralGuardian and mayor of Los Angeles C. Aubrey White turns out to have had a previous career as a transvestite prostitute called 'Lola'. He readopts the Lola guise to murder those who know the truth and can expose the truth

* Played distressingly straight in the otherwise comic [[TheSixties 60s]] caper flick ''Caprice'', in which it’s revealed that [[spoiler:villainous Stuart Clancy got into the fashion industry so he could wear women’s clothes.]]

* The villain of the Hong Kong slasher film ''He Lives By Night'' is a crossdressing serial killer who prowls the streets at night, brutalizing women before strangling them with white stockings.

* Even Film/JamesBond's nemesis Blofeld undertook a spot of cross-dressing (although it was technically a desperate disguise) in the film adaptation of ''Film/DiamondsAreForever''. Also, ''Film/{{Thunderball}}'' has an old enemy of Bond disguised as his own "widow".

* Harry Russo from ''Schizophreniac: The Whore Mangler'' and its sequels, apparently the result of his horribly abusive parents wanting a girl.

* ''Creator/ElleryQueen'': The murderer in ''[[spoiler:The Last Woman is His Life]]'' is one. It is the reveal of him being this (and a DepravedHomosexual) and the victim's reaction that drives him to murder.
* ''Literature/TheMachineriesOfEmpire'', "Extracurricular Activities": Jedao has to [[DressingAsTheEnemy steal a medic's clothes]] during an infiltration IndyPloy, which he does despite the medic being a woman. They keep him from being identified as an enemy operative and he's androgynous enough to [[DisguisedInDrag make the disguise work]], but he keeps getting appalled stares and isn't sure why.
* ''Literature/TroubledBlood'', the fifth installment of the ''[[Literature/CormoranStrikeNovels Cormoran Strike]]'' series by [[Creator/JKRowling Robert Galbraith]], features Dennis Creed, a serial killer who dresses as a woman to lure his victims into a sense of false security ([[spoiler:although he ultimately turns out to be a false lead in the murder investigation at the center of the novel's plot]]).

!!!'''TV Movies:'''
* RealLife head of the Nazi ''Luftwaffe'' Herman Goering was depicted as a transvestite in a 1988 TV Movie, ''The Man Who Lived at the Ritz'', based on A.E. Hotchner's novel.

* Flea from ''VideoGame/ChronoTrigger''. A [[FanWank popular fan theory]] that made it into some fanfic was Flea, being from a race of monsters, doesn't worry about the details of what humans wear so much as wear what he thinks is cute. His official art even has a bust (he wears a push-up bra).

* Gao from ''VideoGame/RhapsodyAMusicalAdventure''. In fact, due no doubt in large part to the graphical limitations of the game, it's actually near-impossible to tell it's a girl. She ends up giving a forced, out-of-place speech about how people can't tell she's a girl just before you fight her simply so the audience can know.
* ''VideoGame/GanbareGoemon'' is rife with these, the most prevalent being Sister Bismaru, Ebisumaru's descendant who dresses like a cross between a [[NunsAreMikos nun and a miko]].
* Justice from ''VideoGame/GuiltyGear'' counts, if only because of the huge crotch spike in her armor...
** There's also the tendency for people to identify mecha as male unless they look distinctly feminine. Even without the crotch spike, she looks sort-of gender-neutral, and thus would likely be identified as male at first glance.
** More obviously, Testament in the first game, which also doubles as the game where his gender is the most ambiguous (thanks to him practicing his VoiceOfTheLegion.) Later games make his gender more obvious and his change in allegiance make him more of a WholesomeCrossdresser.

* ''VideoGame/FinalFantasyTacticsA2'': The Night Dancer is a cross-dressing CampGay ''[[LizardFolk Bangaa]]''. He even wears lipstick (on a Bangaa!) and eyeshadow and refers to himself as female, but fights with him tend to be fought under the "No harming the opposite sex" law, which outs him as male by the fact that female characters attacking him break the law while male characters attacking him do not. (On the other hand, some are so convinced by his insistent female identification that they really believe that he's a she and the law identification is a bug.) [[https://www.youtube.com/watch?v=ibhXqRhxaTU]]
* In ''VideoGame/BlackSigil: Blade of the Exiled'', [[spoiler:Mondu after the world fusion]].

* Examples from ''Manga/FistOfTheNorthStar'':
** Yuda represents the essence of this trope, particularly as played in anime. Outrageous outfit, annoying laugh, and insanely self-absorbed and narcissistic personality. Also obviously, albeit not explicitly, a DepravedBisexual.
** Dekai Babaa is a giant thug disguised as an old woman and tried to give poisoned water to the heroes, but his old lady facade wasn't convincing enough for them.

* ''Manga/OnePiece'' examples:
** Mr. 2 Bon Clay of Baroque Works, the only Baroque Works officer without a female partner, since he counts as both the man and the woman. His alias reflects this, being a combination of a number (traditional for male officers) and and a reference to a holiday (traditional for female officers). [[spoiler:[[DefeatMeansFriendship Though after losing]], he pulls a HeelFaceTurn, like many ''One Piece'' villains, transforming into a WholesomeCrossdresser.]]
** Taken to absurd levels with Emporio Ivankov, the "[[DragQueen queen]]" of Kamabakka Kingdom. His design was modeled on no less than Dr. Frank N. Furter himself. When he was arrested and locked in Impel Down, he founded a Prisoner's Paradise between the prison's two harshest floors where everyone dressed in fishnet stockings and switched freely between genders thanks to Iva's hormone controlling "Horu-Horu" Fruit. When a pirate attacked him, berating him for having transformed his father into a woman and humiliated his whole family, Ivankov transformed ''him'' into a woman too and mocked him, sending him fleeing in tears. And yet despite his absurd level of creepiness, he can still be considered one of the top good guys of the entire ''One Piece'' world, being [[spoiler:a commander of the [[LaResistance World Revolution Army]], just about the ''only'' faction who opposes the corrupt World Government for presumably altruistic reasons (for most pirate crews it's more a case of EvilVersusEvil).]]
** Zigzagged with the inhabitants of Kamabakka Kingdom, the original followers of Emporio Ivankov. They're certainly creepy looking, since they are ''very'' bad at crossdressing--simply throwing on cutesy female clothes and makeup on unshaven and [[{{Gonk}} hideously masculine]] bodies. But they're presented as being fundamentally decent people who don't want to hurt anyone. But then again, they're also very ''bad'' at taking "no" for an answer when it comes to guys not wanting to become "okama" like themselves. And yet at the same time, they were also instrumental in helping Sanji [[TookALevelInBadass get stronger]] during the TimeSkip.
* Kamatari of ''Manga/RurouniKenshin'', though he's portrayed fairly sympathetically and is driven by an unrequited love for Shishio. Otowa, on the other hand, is just a PsychoForHire.

* ''Anime/FullmetalAlchemist'':
** The androgynous but genuinely male Envy has traits of this which were especially played up in the English dub, where his voice is more feminine. This only applies in the 2003 anime, however, as Envy in [[Manga/FullmetalAlchemist the manga]] has no gender (or, according to [[WordofGod Word of God]], no one knows Envy's true gender – not even Envy).
** The serial killer Barry the Chopper first appeared dressing as a woman when out delivering meat from his butcher shop. He kidnapped Winry and [[WouldHurtAChild almost murdered]] both her and Edward.

* The Big Cheese from ''Anime/SamuraiPizzaCats''. Strangely, his flirting with male subordinates was mostly left intact.
* Lady Bat from ''Manga/MermaidMelodyPichiPichiPitch''
* [=McCoy=] from the anime ''Anime/BakuenCampusGuardress'' is a semi-subversion of this trope. He has the laugh, the mascara and the leather dominatrix outfit, he brags about how beautiful he is.... [[{{Gonk}} and he is built like a linebacker]].
* ''Franchise/{{Naruto}}'':
** Orochimaru of ''Manga/{{Naruto}}'', who is actually a man [[BodySurf in a woman's body]] (at the start of the series) ShapeShifting as an effeminate male. Just to make matters creepier, he first shows up wearing a woman's face as a disguise, after ''tearing it off''. Made even worse in an omake where he and his apprentice, Kabuto, show up... [[FanDisservice wearing]] SailorFuku. [[BrainBleach UGAH!]]
** Gai on occasions in ''Manga/RockLeesSpringtimeOfYouth''.
* ''Manga/FlameOfRecca'''s Kurenai may be effeminate, but the real version of the trope doesn't appear until very late in the manga when the clone Aoi poses as a female student. Recca seems unperturbed, considering the much stranger people he's met at this point, except in being completely nonplussed and confused by the [[HeelFaceTurn reformed]] Aoi trying to explain his complicated backstory.
* ''Manga/{{Monster}}'' offers a particularly creepy example in which this trope is '''not''' played for laughs. [[spoiler:Johan impersonates his twin sister, Anna, in a flawless fashion that is quite disturbing. He still manages to sound threatening while wearing a dress, which says a ''lot'' about how ultimately creepy he can be. Interestingly, the creep factor doesn't come so much from the gender implications so much as how much it represents his concept of himself and Anna as the same person.]]
* ''Manga/{{Bleach}}'':
** Charlotte Chuhlhourne is a flamboyant MagicalGirl parody. His normal attire may involve trousers, but he wears a tight tank top with plunging, frilly neckline and bared midriff, and his trousers expose the tops of his thighs on each side as well as revealing a little too much of his [[FanDisservice pelvic area]]. His hair is very long and painstakingly curled and styled and he wears long, false eyelashes. In his Resureccion form, called ''Reina de Rosas'', he transforms into a frilly, bikini-style tutu costume that is designed with the petals of a [[FlowerMotif rose]] in mind. He's extremely proud of his [[MachoCamp muscular strength]] and his costumes are designed to show off his body as much as possible.
** Giselle is accused of being a man by Yumichika but neither confirms nor denies the accusation. While she actually dresses in a quite wholesome-looking fashion, the more that's revealed about her, the less wholesome she appears. [[spoiler:Yumichika claims she reeks of semen, and a [[TheUndead resurrected]] Charlotte also identifies her as "[[DragQueen resembling]]" him after sniffing her. Giselle creates zombies by infecting shinigami with her blood and even kills her Quincy friend Bambietta to turn her into a zombie. She drools when excited and the thought of using her blood on others seems to turn her on.]]
* ''Anime/{{Pokemon}}'' loves crossdressing villains:
** Team Rocket, most of the time: In Kanto and Johto, Jessie would crossdress as a male (complete with mustache), while James crossdressed as a female at the same time. Perhaps the most disturbing example is the infamous "bikini contest" episode, where James has a pair of inflatable breasts that led to the episode being banned. Amusingly, no reason was ever given why they couldn't just disguise themselves as their own gender.
** Harley is also a great, albeit much less permanent, example, but technically he only crossdresses once.
* ''Manga/JoJosBizarreAdventure'':
** Narciso Anasui from ''Manga/StoneOcean'' might classify as this depending on who you ask, given his SociopathicHero nature. But he is technically part of the "good guys", so he might be in a different category of [[WholesomeCrossdresser crossdresser]].
** Despite what his name may suggest, [[GenderBlenderName Mrs. Robinson]] from ''Manga/SteelBallRun'' is both a crossdressing man and one of the creepiest [[StarterVillain Starter Villains]] of any Part.
* ''Anime/CodeGeass'' examples:
** Earl Kanon Maldini, the aide to Prince Schneizel. In the series, he is not shown as a crossdresser (but he ''is'' [[AlwaysCamp feminine looking enough]] and once jokes about [[SubordinateExcuse aiding]] [[HoYay Schneizel]] in "his private affairs" as well), but [[AllThereInTheManual the Code Geass novels]] not only say he is, but that he [[TruthInTelevision was persecuted for it]] until he met Schneizel and was hired as his assistant.
** Lelouch does this at least twice in the picture dramas. In one of them, the Student Council has a crossdressing festival, so everyone crossdresses (and Suzaku mentions having done it a few times before).
* Tsubasa Kurenai from ''Manga/RanmaOneHalf''. A straight guy who dresses up like a schoolgirl and relentlessly stalks former schoolmate Ukyo Kuonji (a straight girl who spent most of her life [[{{Bifauxnen}} dressing up like a guy]]) while disguised as various inanimate objects. Tsubasa is assumed to be a lesbian at first because he's ''very'' passable and is only interested in women. Ranma tries dating Tsubasa while in male form to set "her" straight, only to find that Tsubasa [[UnsettlingGenderReveal is a boy]].
* Mariya from ''Manga/MariaHolic'' does a very convincing job as a girl. Since this is an all girls' school, no surprise that he gets Kanako falling for him the moment they meet. He's also incredibly sadistic.
* One early example of this trope would be Rock, from the various manga by Creator/OsamuTezuka. Who, in his more villainous incarnations, would often disguise himself as a woman.
* Yuuji Fukunaga from ''Manga/LiarGame'' starts off as this, but slowly pulls a HeelFaceTurn and becomes one of the main supporting characters while still making a better looking girl than most of the female cast combined.
* The ''Franchise/{{Kirby}}'' [[Anime/KirbyRightBackAtYa anime]] has Escargon, a CampGay villain with a not-so-subtle crush on his boss who has crossdressed a few times (usually because said boss wanted him to).

* ''Anime/GhostInTheShellStandAloneComplex'' has a special case in which [[spoiler: Pazu's]] PsychoExGirlfriend wants to kill him and take both his cybernetic body and his identity. [[spoiler: Fortunately, the real Pazu won. There are just enough clues at the end of the fight to prove it.]]
* [[spoiler:[[CreepyChild Sakurako]]]] from ''Manga/SakuraGari'' [[spoiler:is actually Souma's brother, named Youya. He stole his mother's name and dressed in her clothing after she died, having been traumatised after witnessing said mom's murder at the hands of Souma and Katsuragi. Soon after his gender was discovered by Masataka, he tried to kill both him and Souma, then had a heartbreaking VillainousBreakdown and [[DrivenToSuicide committed suicide]].]]
* [[EvilTwin Rosiel]] from ''Manga/AngelSanctuary'' often [[IncrediblyLamePun skirts]] the line with his ''[[FashionVictimVillain unusual]]'' outfits. AntiVillain [[{{Bifauxnen}} Belial]] also counts.
** PlayedForDrama with [[spoiler:[[SamusIsAGirl Sevothtarte]]]].
* Chapter 279 of ''Manga/AirGear'' reveals that the villainous loli Shalott who dresses in a frilly dress and wears a NiceHat is [[UnsettlingGenderReveal actually a guy]].
* [[CreepyTwins Hansel and Gretel]] of ''Manga/BlackLagoon'' are very fond of swapping clothes (and, more disturbingly, ''personalities'') with each other. Which one's which gender, though, is [[AmbiguousGender anyone's guess]].
* ''Manga/BlackButler'': In episode five of the second season, [[CuteAndPsycho Alois Trancy]] dresses up as a maid to lure Ciel into his bedroom so he can flirt with him and take his eyepatch. It's also shown that he has a few dresses in his wardrobe.
* "Miss Aki," an unattractive example from ''Anime/MagicalShoppingArcadeAbenobashi''.
* Count D in ''Manga/PetshopOfHorrors'' is good friends with a group of drag queens and transvestites, and his peacocks also appear this way in their 'human' forms.
* The bad guy in ''Anime/LupinIIIThePursuitOfHarimaosTreasure'' was [[ThoseWackyNazis Herr Maphrodite]], who doubles as a SissyVillain and EffeminateMisogynisticGuy, as well. The clothing and behavior during the villain scenes made him creepy long before we find out who he really is.
* Michio Yuki of manga series, ''Manga/{{MW}}'', cross-dresses as his female victims after killing them.
* In ''Manga/MyBrideIsAMermaid'', Both Sun and Lunar's fathers try to get to know their daughters a little better by exploring some research into teenage life (I.E: they explored a goofy DatingSim). The end result completely horrifies ''EVERYONE'' else, especially the two girls. Seeing the anime equivalent of the Franchise/{{Terminator}} wearing a sailor fuku is not a pretty sight. Funny, but not pretty.
* Baikinman from ''Literature/{{Anpanman}}'' will commonly disguise himself as characters to either get the character he's disguised at in trouble, or to get free food out of people. Most of the time, he'll end up disguising himself as some of the female characters...even if Dokinchan is with him. When he disguises as a female character, Dokinchan will either crossdress as a male character that works with the female character, or even sometimes make up a male counterpart to the existing female character.
* ''Anime/AnoHanaTheFlowerWeSawThatDay'': A more tragic example. After the death of his childhood love, Menma, Yukiatsu takes to dressing up as her and running around their childhood hangout at night. This is his way of coping with his loss.
* Kaito from ''Manga/HimegotoJuukyuusaiNoSeifuku'' comes off as this at first. He is a man who enjoys dressing up as the woman he has a crush on, a {{Jerkass}} who toys with women's emotions, pretended he was going to rape Yuki, and generally acts manipulative and sly. However, the further the manga goes the more it becomes obvious that Kaito is more likely UsefulNotes/{{Transgender}} than just a villainous crossdresser. His obsession with Mikako is creepy, however, a lot of things he does happen out of fear for not being accepted the way he is. The time he spends with Yuki as his girl persona he is a genuinely caring and nice person, albeit somewhat pushy. And the women he goes out/sleeps with to get money so he can afford his other life as a girl are middle-aged women who sleep with a 19-year-old to prove to themselves they're still desirable. He is sly and manipulative, but actually pales in comparison to his crush Mikako.
* Osamu from ''Manga/BokuraNoHentai'' has shades of this. He's portrayed as less emotionally stable than the other crossdressers.
* Izumi from ''Manga/BokuToBoku'' isn't too villainous but he's portrayed as a perverted, more mean spirited foil to the WholesomeCrossdresser Jun.

* Even ''Franchise/PrettyCure'' got in on this, as [[Anime/HappinessChargePrettyCure Phantom, the Pretty Cure Hunter,]] went into battle as Cure Un-Lovely, a Cure Lovely lookalike dressed in [[RedAndBlackAndEvilAllOver red and black]], in one episode.

* Baikinman from ''Franchise/{{Anpanman}}'' will commonly disguise himself as characters to either get the character he's disguised at in trouble, or to get free food out of people. Most of the time, he'll end up disguising himself as some of the female characters...even if Dokinchan is with him. When he disguises as a female character, Dokinchan will either crossdress as a male character that works with the female character, or even sometimes make up a male counterpart to the existing female character.

* Kamek from the ''Franchise/SuperMarioBros'' series dons Princess Peach's dress and a wig as a disguise in both ''VideoGame/NewSuperMarioBrosU'' and ''VideoGame/MarioAndLuigiDreamTeam''....and, in the latter, accidentally confirms that he likes wearing the dress. ''VideoGame/MarioAndLuigiPartnersInTime'' also sees him wearing a frilly, white lace apron over his usual robe.

* ''VideoGame/PlantsVsZombies2ItsAboutTime'': In the Zombot Multi-Stage Masher fight, Dr Zomboss stands on a stage and changes his clothes to fit the current Jam. During the Pop Jam, he dresses up like a popstar girl with a dress and red wig. Take note that Zomboss is a diminutive male zombie with an [[MyBrainIsBig oversized brain]].

* Elendira the Crimsonnail from ''Manga/{{Trigun}} Maximum'' (the later volumes of the manga), although he or she is most likely a {{transgender}} woman.

* Kaito from ''Manga/HimegotoJuukyuusaiNoSeifuku'' comes off as this at first. He is a man who enjoys dressing up as the woman he has a crush on, a {{Jerkass}} who toys with women's emotions, pretended he was going to rape Yuki, and generally acts manipulative and sly. However, the further the manga goes the more it becomes obvious that Kaito is more likely {{Transgender}} than just a villainous crossdresser. His obsession with Mikako is creepy, however, a lot of things he does happen out of fear for not being accepted the way he is. The time he spends with Yuki as his girl persona he is a genuinely caring and nice person, albeit somewhat pushy. And the women he goes out/sleeps with to get money so he can afford his other life as a girl are middle-aged women who sleep with a 19-year-old to prove to themselves they're still desirable. He is sly and manipulative, but actually pales in comparison to his crush Mikako.

* [[spoiler:Marube]] from ''Manga/{{Yuureitou}}'' is obsessed with [[IJustWantToBeBeautiful becoming beautiful]] to the point where he would do anything to become a female [[spoiler:including attempting a brain transplant with his [[{{transgender}} son]] Tetsuo.]] In his final appearance he's dressed as a woman, and a very attractive one despite [[OlderThanTheyLook being in his forties]], but is very unhinged.

* In ''Literature/{{Parrotfish}}'', some football players dress up in drag at the start of a game. It's supposed to be funny and is supposedly a long-standing tradition, however Kita finds it an offensive TakeThat against Grady (who is a {{trans|gender}} boy).

* In ''VideoGame/SaintsRow2'', ''VideoGame/SaintsRowTheThird'', and ''VideoGame/SaintsRowIV'' the player can dress their character in any clothes in the game, regardless of gender. So the player can make their character a transvestite, or even a {{Transgender}} through EasySexChange, if they so desire. This can go into "Creepy" territory instead of "[[WholesomeCrossdresser Wholesome]]" by having a hugely muscled man running around in a tiny dress or worse/more hilarious a string bikini and beating random passerby's to death with [[WrestlerInAllOfUs wrestling moves]] and [[GroinAttack nut punches]] when he isn't blowing their brains out or running them over in a tank. In the third game, there's also a [[GiantMook Brute]], an 8-by-4 foot mountain of muscle, dressed like a naughty schoolgirl in the dungeons of a S&M sex club. There is no context for it being there outside of the club is run by [[BigBad the Syndicate]] and it's funny.

* In ''WesternAnimation/TheSimpsons'', episode "There is Something About Marrying", pro golfer Veronica was going to marry Patty under the false pretense of being a lesbian woman. (It's somewhat unclear, but Veronica doesn't seem to be a genuine {{Transgender}} so much as a creepy male golfer who only crossdresses so that he can compete on the womens' tour.)

* ''LightNovel/AscendanceOfABookworm'' has Justus, a SeekerArchetype who has channeled his great hunger for information and willingness to go to great lengths to obtain it into doing spy work. Since he lives in a society with a decent amount of gender segregation, there are some places he can't go without making use of DisguisedInDrag. If his willingness to do so gets any in-universe comment, it's treated as one of his bigger quirks among the laundry list he has accumulated in the midst prioritizing information gathering over several social norms. One of such comments comes from the protagonist, who switches from not wanting Justus in her orphanage without their shared CloudcuckoolandersMinder to watch him to not wanting him inside it at all when he seriously offers to cross-dress to avoid making the DoesNotLikeMen adult residents of the girl's building uneasy.