New glamour dress on a male (art)

[Pomelo]

you kinda missed the point.
female fits in male clothes, cause male clothes are uni-sex, fem clothes aren't.
A guy would need to transgender, to fit into fem clothes, while she doesn't have to; She could have skipped the facial hair, and been Jackie Sparrow.

I just want to pipe up and say ALL clothes are unisex. Its society that chooses and labels what gender fits into what. This isn't even about being transgender lol.

[kyuven]

I just want to pipe up and say ALL clothes are unisex. Its society that chooses and labels what gender fits into what. This isn't even about being transgender lol.

I disagree.
It would be really uncomfortable to wear a bra and thong bikini as a man. It's only unisex if it actually fits the body's proportions.
A t-shirt is generally unisex, but many jeans are not because they're designed for specific types of proportions. Namely...the tight ones for women are not designed with the man's equipment in mind.
Society may have its say into it, but basic tailoring, physics, and biology apply as well. There will always be specific fits and appearances that work for one gender but not the other.

I don't know if I already posted this but all races and all genders in Lord of the Rings Online can crossdress and one would think that Middle Earth would be more strict about things than here? XD

American game (based on material by a British author but whatever)
You can also crossdress in World of Warcraft with certain armor pieces. That's another American game.
Those are kind of the exception that makes the rule, though. A LOT of games with surprisingly deep character customization such as Champion's Online don't allow crossdressing either (just like here, all or most of their "skirts" available for males are either related to magic casting, priesthood, or kilts)
Sooo...it's really hit or miss, y'know?