Is it socially acceptable for individuals to wear clothing typically associated with the opposite gender? What are some reasons for or against this practice?

a) In serious entertainment, actors playing a role. From Mark Rylance as Cleopatra or Judi Dench as Olivia to Antony Perkins in Psycho. Japanese Kabuki and Nō players. Sopranos singing "breeches" roles in opera.

Reasons against it? Basically,

Socially acceptable? It depends on which bit of society you live in.

Have you ever met someone and something seemed so unusual about them but you couldn't put your finger on what it was?

If it’s merely your sexual fetish — see 3) above — don’t do it in public. You’ll look ridiculous and possible offend decency laws.

2) Fashion crossdressers - some metrosexuals and most women fall into this category. Women in trousers – seen as a sexual and social aberration in 1900 – had become the norm by 2000.

5) Other professionals: the occasional spy/undercover policeman/criminal in disguise. Gay prostitutes.

I want to have anal sex, but my wife refuses. What do I do?

d) Stunt doubles.

1) Occasional crossdressers - Hallowe'en, practical jokers, fancy dress parties, students' rags... etc.

In Lancaster County, Pennsylvania or Salt Lake City it won’t be accepted. In Rio or Douarnenez at Mardi Gras it’s practically compulsory. (Seriously, I counted the men in skirts in a bar in Douarnenez: one in six.)

What is the Abu Shusha massacre in Palestine?

Ignore people who will quote their religion at you (unless it’s your religion too).

There are many reasons. This can be broken down into the eight broad categories below, though most people only think of no.6:

3) Fetish crossdressers - who use clothes as a substitute for, or an essential precursor to, sex. This is commonest among teenage boys, but usually disappears or develops into transvestism later. It is rarely seen in public, although the word "fetish" is often misapplied by those who should know better.

What are some alternatives to wearing a bra? Why do some women feel pressure to wear bras even though there may not be any benefits?

7) Transsexuals – for many of them the cross-dressing is merely an incidental stage in their transition of identity. Once achieved, the wearing of the clothes of the other sex becomes the norm, and can no longer be called crossdressing.

If you’re going to do it, do it 100% and do it well. You’ll enjoy it all the more and so will the people around you. It’s often good for a round of applause or a free drink.

c) Drag queens and Drag kings – an exaggerated satirical sub-section of the light entertainment field.

Why do black people prefer thick, curvy women?

Don’t do it in places where it’s illegal, like Russia.

8) Those forced into crossdressing. This category is included for completeness but barely seems to exist in real life today. It was however observed in the period 1850-1950 when boys were occasionally forced into girls' clothes as a punishment at school or in the home. It is a staple of fiction – to escape from danger (Some Like It Hot), to obtain a job (Tootsie, Mrs Doubtfire), or forced by a sadistic female relative (much transvestite erotic fiction).

4) Entertainers.

When does a woman know she is cumming?

Don’t do it unless you want to.

b) In light entertainment: female impersonators/comedians; pantomime dames in British theatre.

6) Transvestites – what most people first think of. For transvestites, crossdressing is an end in itself; motives many and various. For most, these go back to childhood or before birth and are obsessive.

What is the reason behind the Russian government's negative view on foreign travel?