History Main / Crossdresser

* Fanfic/KhaosOmega is known to implement scenarios that involve crossdressing, one of them a tweaked case of Kazuya's crossdressing in the first game of the ''Galaxy Angel II'' trilogy. Here, the tweak is that Lily tries a longer-range approach to remove Kazuya's maid attire but botches it; a far bustier Anise, who had seen it coming, convinces Kazuya to resume crossdressing, which he does more passionately. Anise herself is later revealed to be the primary Alpha of a massive harem whose leader, Jet Brazie, has a special gender status allowing him to cross-dress without it being identified as such (he doesn't go fully until 2550 following the capture of Tracy Dennis), which Kazuya (his role in triggering Anise and Jet's marriage without an actual wedding, due to buying Anise her FairytaleWeddingDress), Jace Davies (a transformation-induced Chaos Reaction near his own Anise), and Jayden Omega (a sixth birthday present) also obtain. Jet's case is later replicated by a Cloud Strife who had previously met Anise during her [[VideoGame/SuperSmashBrosUltimate World of Light mission]], in which he'd been one of five [[Rule34 caught up in the shenanigans of Anise's then-problematic Meme Storm]], but switching elemental affinity from Ice to Lightning (presumed to be one of the decisions that result in [[ContrivedCoincidence the second convenient naming chain regarding a second-generation member of Anise's Amethysts]].

!!! Tropes about other character's responses:

* ''Series/{{Mash}}'': Corporal Klinger, in attempt to prove that he is clinically insane and therefore unfit for active duty, regularly shows up in some form of women's dress, right down to the earrings and slip. Unfortunately, he can't pull off "crazy" because his personality is still the same.

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[[folder: Comedy]]

[[folder: Fan Works]]

[[folder: Films -- Live-Action]]

[[folder: Literature]]

[[folder: Live Action TV]]

[[folder: Webcomics]]
* {{Averted}} with Tedd in ''Webcomic/ElGoonishShive''; he may own more skirts than his girlfriend, but he [[GenderBender doesn't wear them as a boy.]]

[[folder: Web Animation]]

[[folder: Western Animation]]

* Jessie and James, members of Team Rocket from ''Anime/{{Pokemon}}'' were shown to cross dress frequently whenever they go in disguise with Jessie sometimes dressing up as a man and James dressing up as a woman. James in particular has cross dressed way more than Jessie has as he dressed himself up as a schoolgirl, a ballerina, and even went as far as buying fake breasts and entering into a beauty pageant with them, which caused an episode of the series to get banned because of him. This characteristic died down as the series progressed.

[[folder: Film]]

* ''VideoGame/ValkyriaChronicles4'': Handled in a refreshingly tasteful manner for a Japanese game. The specific details of Rosetta's gender and sexuality are not clear, but it is clear that she considers her feminine attire to be cross dressing. This is not played for laughs or even mentioned at all - nobody in Squad E seems to care one way or another.

See also AmbiguousGender, ViewerGenderConfusion, {{Bishonen}}, {{Bifauxnen}}, and DudeLooksLikeALady, tropes which share some common aspects with the above but generally are not about deliberate crossdressing. Similarly, UnplannedCrossdressing technically involves crossdressing, but it's unintentional on the character's part. Like DragQueen, CrosscastRole involves crossdressing, but only in the context of "performance" -- here, an actor playing a part.

* ''Film/GlenOrGlenda'' was director Ed Wood's personal passion project to explain and legitimize cross-dressing, which he enjoyed. Glen, the main character, enjoys cross-dressing in secret, but must figure out a way to explain this to his fiancé Barbara before the wedding. Although this movie is known as SoBadItsGood, you have to admire the courage Wood had to make this film back in the early 50s, when cross-dressing was considered a shameful secret weird fetish.

See also AmbiguousGender, ViewerGenderConfusion, {{Bifauxnen}}, and DudeLooksLikeALady, tropes which share some common aspects with the above but generally are not about deliberate crossdressing. Similarly, UnplannedCrossdressing technically involves crossdressing, but it's unintentional on the character's part. Like DragQueen, CrosscastRole involves crossdressing, but only in the context of "performance" -- here, an actor playing a part.

* Kazuya Shiranami of Galaxy Angel is stated as having been forced to cross-dress before he joined the Rune Angel Wing. In the first game of the Galaxy Angel II trilogy, in what becomes Natsume Izayoi's route, he finds himself forced into it once more, as a maid with Grade A ZettaiRyouiki. This situation piques the curiosity of Anise Azeat when she sees him (as both Kazuya and the cross-dressed Katherine, on separate occasions) sneaking around; it's in a scene where the female Angels are undressing that Lily finally busts him.
** In the third game of the Galaxy Angel II trilogy this nearly happens to Kazuya again (again in Natsume's route, here affecting Kazuya whereas the tomboyish Anise is the one affected in her route), but Lily quickly neutralizes the cause to protect Kazuya's so-called secret.
* [[spoiler:Kaoru Kamata]] of ''Manga/ShonanJunaiGumi'' can seem like both a CreepyCrossdresser and a WholesomeCrossdresser at times. He likes to dress up as a woman and invite guys back to his place, only to then change into a man in the bathroom and beat up the guys for trying to take advantage of his "sister". However, he then falls for Eikichi, [[LoveAtFirstPunch after Eikichi is the first guy to beat him up]].

* Fanfic/KhaosOmega is known to implement scenarios that involve crossdressing, one of them a tweaked case of Kazuya's crossdressing in the first game of the Galaxy Angel II trilogy. Here, the tweak is that Lily tries a longer-range approach to remove Kazuya's maid attire but botches it; a far bustier Anise, who had seen it coming, convinces Kazuya to resume crossdressing, which he does more passionately. Anise herself is later revealed to be the primary Alpha of a massive harem whose leader, Jet Brazie, has a special gender status allowing him to cross-dress without it being identified as such (he doesn't go fully until 2550 following the capture of Tracy Dennis), which Kazuya (his role in triggering Anise and Jet's marriage without an actual wedding, due to buying Anise her FairytaleWeddingDress), Jace Davies (a transformation-induced Chaos Reaction near his own Anise), and Jayden Omega (a sixth birthday present) also obtain. Jet's case is later replicated by a Cloud Strife who had previously met Anise during her [[VideoGame/SuperSmashBrosUltimate World of Light mission]], in which he'd been one of five [[Rule34 caught up in the shenanigans of Anise's then-problematic Meme Storm]], but switching elemental affinity from Ice to Lightning (presumed to be one of the decisions that result in [[ContrivedCoincidence the second convenient naming chain regarding a second-generation member of Anise's Amethysts]].

[[folder: Web Comics]]

* Sock from ''Webcomic/WelcomeToHell'' wears a SkirtOverSlacks. This doesn't get mentioned in-series. On one hand, Socks is a demon in hell whose job is to make people DrivenToSuicide. On the other hand, he [[MinionWithAnFInEvil completely sucks at his job]] and seems more like a plucky {{keet}} than a villain.

See Also AmbiguousGender, ViewerGenderConfusion, {{Bifauxnen}}, and DudeLooksLikeALady, tropes which share some common aspects with the above but generally are not about deliberate crossdressing. Similarly, UnplannedCrossdressing technically involves crossdressing, but it's unintentional on the character's part. Like DragQueen, CrosscastRole involves crossdressing, but only in the context of "performance" -- here, an actor playing a part.

* ''Series/NightAndDay'''s Fiona Brake and Dennis Doyle both have forays into cross-dressing; Fiona in a bid to seduce her gay husband, and Dennis because he briefly thinks he might be intersex. Also, in in the final episode, set four years into the future, we learn that Ryan Harper now wears women’s clothes and goes by the name of Beverly.