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

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

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.

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.

Is it better for 2nd generation Western Muslims to marry someone from their parents' country or a western Muslim who was born and raised in the West?

d) Stunt doubles.

4) Entertainers.

Reasons against it? Basically,

Why do philosophy of physics when you can do physics itself? - Aeon

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

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.

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

Tour players, a 17-year-old and a dentist among those who qualify for U.S. Open on Golf's Longest Day - NBC Sports

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.

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).

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.

SpaceX knocks out another national security launch while ULA faces scrutiny - Yahoo

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

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.

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

Have you made a female relative or friend squirt?

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

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.)

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

Tender Moment Nurse Mare Adopts Orphaned Foal As Her Own Has Us in Tears - Yahoo

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.

Don’t do it unless you want to.

This Cat Poop Parasite Can Decapitate Sperm—and It Might Be Fueling Infertility - Gizmodo