There's little approval of actual individuality. OTOH, "individuality" is all the rage. It's not what it's made out to be. Particular little perturbations around accepted things are ok, but actual deviation is just, you know, freakin' weird & unacceptable.
As with most things human, I think it comes down to social status & positioning. With (some) fashion, I think the idea is to make things ridiculous enough that people want to laugh, but subtle enough that they won't if others seem to be taking it seriously. That set-up makes out the laughers to be too un-cool "get it."
So people won't laugh, but will instead insecurely wonder about the mysterious, sophisticated fashion-sense that they lack; the secret knowledge that separates them from the Cool People. But then, they don't have to have it -- they can pretend to, and thereby be cool, even though it really makes no sense to them. Of course, the punchline is that nobody really gets it and that everyone is pretending to in order to impress everyone else.
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Aspie Quiz: 160/43
Alien Quiz: √2/pi