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

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

Don’t do it unless you want to.

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

Should any books be banned from school libraries? Why is it important for students to read certain books in school?

4) Entertainers.

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.

d) Stunt doubles.

Has Trump fooled Canadian PM Carney by pretending to negotiate and suddenly doubling steel tariffs to 50%?

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.

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.

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.

French Open 2025 results: Jannik Sinner cruises into semi-finals with victory over Alexander Bublik - BBC

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).

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

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

Junk Food Alert: Our Bodies Treat Ultra-Processed Foods Like Foreign Invaders! - Glass Almanac

Reasons against it? Basically,

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.

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

Your chatbot friend might be messing with your mind - The Washington Post

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.)

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

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.

What makes Nigerian scammers skilled at impersonating people? Is their success a result of intelligence or other factors?

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

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

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.

Why do most people care so much about what others think? Are they afraid of society norms?