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

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

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

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.

Can omega-6 fatty acids in nuts, vegetable oils lower heart disease and diabetes risk? - Medical News Today

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.

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

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

Why prices from these cities in Utah and Nebraska won't be included in inflation data - NPR

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

d) Stunt doubles.

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

Why does my narcissistic ex told me that he f*cked and sleep with other woman and then at the end says that it also happened because of me?

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).

Reasons against it? Basically,

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

How does gut health affect mental well-being?

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.

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.

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.

How can you maintain self-control?

4) Entertainers.

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.)

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.

Why The Simpsons stopped producing Maude Flanders episodes?

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

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.

Don’t do it unless you want to.

Can a cop pull you over walking home asking why you are out so late?