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|Spectra and binaries|
“”No, these aren't women's clothes; they're my clothes. I bought them.
|—Eddie Izzard, with regards to wearing "women's" clothing during performances|
Cross-dressing (sometimes referred to as transvestism, although this term is largely considered obsolete and pejorative nowadays) is the preferred term for dressing in a manner generally associated with a gender other than the one one self-identifies as. People may have various reasons to cross-dress such as sexual excitement and/or relaxation
Relationship with transsexuality
Persons who identify with a gender which differs from their sex assigned at birth are transgender. They may dress as anyone else in their gender would without being a crossdresser (if you're dressing as the gender you identify with, it's by definition not cross-dressing).
Still, many self-identified cross-dressers are trans people whose circumstances do not yet allow them to transition - maybe they live with family who isn't supportive, maybe they're underage, maybe they just aren't really in a position to accept the social consequences of transition. It can seem easier in the beginning for a trans person to use the language least likely to lead to negative social consequences, and thus identify as a cross-dresser, considering this more socially acceptable. This does not mean that cross-dressers don't exist, or that all trans people have identified as cross-dressers. There's an old joke in parts of the trans community that a transvestite is a trans woman minus two years, but in practice they're different forms of gender variance that happen to overlap sometimes.
Relationship with homosexuality
As Ed Wood went to great pains to explain in his masterpiece, Glen or Glenda, "transvestites are not homosexuals". They can be, but the two aspects are separate and only tangentially related. Dressing in drag (an exaggerated, campy form of gender performance which is not the same as everyday cross-dressing, where the aim is to "pass" for the other sex) is popular among gay men. There are many drag-themed cult movies that have a following with gay men, and drag balls (events where people are encouraged to come in drag with a contest for the best costume) are common around Pride Week and stuff like that. Nevertheless, a man who dresses in drag is not the same as being transgender. As RuPaul put it: "How many women do you know who wear seven-inch heels, four-foot wigs, and skintight dresses? I don't dress like a woman; I dress like a drag queen!"
Relationship with feminism
This is mostly dependent on who you ask. To some people, the idea of gender-specific clothing is not compatible with the ideals of feminism, while to others it is. Undoubtedly, men who cross-dress for the purpose of mocking women are incompatible with the ideals of feminism, but of course most cross-dressers don't cross-dress to mock women. There is also a double standard at work here: while a woman now wearing a pantsuit isn't exactly shunned or frowned on in the modern era, a man who wears a skirt is (at least in the West, and outside Scotland), due to society's disparagement of femininity and femaleness.
Relationship with psychology and psychiatry
Historically, cross-dressing (called transvestism as a clinical term) was pathologized by the medical establishment and considered a disorder stemming from Freudian sexual conflicts. Today, cross-dressing is widely considered a harmless form of gender expression by experts in the field, but the diagnosis of "transvestic fetishism" still exists in the DSM-5 even though the mental health profession has mostly moved on from the idea that all cross-dressing is sexual in nature and problematic. The term "transvestite" itself is often considered derogatory for these historical reasons; "cross-dresser" is preferred.
Cross-dressing and the Bible
Not surprisingly, this is another abomination. :
A woman must not wear men’s clothing, nor a man wear women’s clothing, for the Lord your God detests anyone who does this.
- Eddie Izzard
- Ed Wood
- J. Edgar Hoover — or was this just a rumor started by the KGB?
- Rudolph Giuliani — and there are photos to prove it!
- Sergey Brin — co-founder of Google.
- Tim Berners-Lee — founder of the World Wide Web.
- Twiggy Ramirez, which is what led to some of the fundie rumors of the 1990s.
- The Monty Python Lumberjack, and pretty much everyone else in the troupe.
- The New York Dolls
- Dame Edna, Danny la Roux, RuPaul, Lily Savage
- Grayson Perry, artist
- David Bowie, or at least his various alter egos.
- Tim Curry and Anthony Stewart Head
- "Drag Isn’t Like Blackface. But That Doesn’t Mean It’s Always Kind to Women."
- Like this one. And this one with Donald Trump. And this one. And this one.
- http://www.digitaldreamdoor.com/pages/lyrics2/nov_lumberjack.html lyrics here
- Though, like Eddie Izzard I much prefer the term executive transvestite.