"Whatever happened to Fay Wray?
That delicate satin-draped frame
As it clung to her thigh
How I started to cry
'Cuz I wanted to be dressed just the same"

In short, this trope is about "dressing in the clothing of the opposite sex." The long version can get a little more complicated.

Crossdressers may be men dressing as women, or women dressing as men. Contrary to popular belief, crossdressing does not necessarily imply homosexuality. An element of sexual arousal ("transvestic fetishism") may be involved in dressing, but not necessarily. And sometimes the primary purpose for crossdressing is simply disguise. This supertrope covers all the various possibilities and permutations.

Distinguished from Drag Queen, which tends to be strongly associated with gay men and has an inherent aspect of "performance." Also not to be confused with Transsexual, which describes a people who consider themselves to be members of the "opposite" sex. There's always potential for overlap, however. A drag queen may also dress as a woman while "offstage," and thus be a crossdresser as well. Some people may start out as "merely" crossdressers, only to eventually discover that they are truly transsexual.

"Crossdresser" and "Transvestite" aren't necessarily synonymous in Real Life. Many different (and often contradictory) definitions for each term can be found. This trope is intended to encompass all of them — at least for purposes of troping.

Note that, since the 1960s or so in western culture, there tends to be little or no social stigma attached to women wearing "traditionally male" clothing. Once upon a time, however, a woman dressing like a man (e.g., wearing trousers) would be frowned upon, or even illegal in some jurisdictions.

The following are subtropes of Crossdresser:

Tropes about characters and their clothing choices:

Tropes about dressing as disguise:

Tropes about other character's responses:

See Also Ambiguous Gender, Viewer Gender Confusion, Bifauxnen, and Dude Looks Like a Lady, tropes which share some common aspects with the above but generally are not about deliberate crossdressing. Similarly, Unplanned Crossdressing technically involves crossdressing, but it's unintentional on the character's part. Like Drag Queen, Crosscast Role involves crossdressing, but only in the context of "performance" — here, an actor playing a part.


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     Anime & Manga 
  • Ryou and Osamu from Bokura no Hentai don't fit either Wholesome Crossdresser or Creepy Crossdresser completely. While originally The Bully and disgusted at the other protagonists, Ryousuke is presented quite sympathetically due to his back story and poor home life. Osamu is presented as something of a Wholesome Crossdresser early on but quickly goes down a slippery slope of unsettling behavior and depression.
  • Kei Shimura of High School Ninja Girl, Otonashi-san doesn't crossdress out of any desire to be seen as female, nor with any true villainous intent. He only does it because femininity is the only area in which he can surpass his rival, the title character Fuka Otonashi.

     Live Action TV 
  • British television has a proud tradition of men dressing as women for comedy. It probably goes back to how men (or boys) played female roles in Shakespeare's day; re-enforced by their tradition of single-sex schools (few plays have all-male or all-female casts, so if a single-sex school has a drama program AT ALL, SOMEBODY will get cross-cast.) Some have gone so far as to say that there is nothing funnier to a British audience than a man dressed up like a woman.
  • Coronation Street , of all programmes, had a particularly bizarre plot-line involving Audrey Roberts and a transvestite boyfriend....
  • In Princess Returning Pearl Xiao Yan Zi and Zi Wei sometimes dress as male when going outside. No one is fooled.

     Web Comics 

     Western Animation 
  • Never shown but there are a few jokes in The Weekenders that imply Carter crossdresses.

Alternative Title(s):

Transvestite, Crossdressing