I'm all for individuality. I really am.
One of the things I love most about my sister is that she lets my niece dress however she wants - which meant pink shorts, a blue and purple shirt with an orange design, and green, yellow and pink argyle knee-high socks last week. I love that my 6 year old niece is confident enough to express herself how she wants and not be intimidated or pressured into following trends or crowds. My sister told her the other day that she looked like Punky Brewster (we always tell her that) and she replied "Punky Brewster was like 40 years ago and you're still talking about her, right?"
I asked her once if anybody in her class laughs at her and she said that if they do, it's just because they want to be like her and don't have the skill to pull it off.

Yeah, I love that kind of confidence. I never had it as a kid and I don't have it now. But I think there's a limit... I'd have to draw the line at letting my kid cut all her hair off. That's just going too far.