Well, I'm growing my hair out now. I'm going for the folkloric look, hehe. I asked my mother if I dressed too young. She said she thought I can wear what I want because my behaviour is somewhat ageless... although I probably would look really funny hanging out with the 20 year old anime types at the next table over. To which I had to say, I just can't do a Hello Kitty in the rear window of my Civic, this much is true.
Anyways, I think it's done best with a modernistic cut. Something coiffed a la Margaret Thatcher 1980 is a little aging - which is beneficial to a conservative PM but not so much others. IMHO.
Should still be neat tho, I feel. The windblown beachy look, I don't know about that. I'd rather see it up in situations like that. Maybe a Prairie House influence on my feelings - mature women put there hair up. Anybody remember when Laura hit, what, 16 and put her hair up in a bun for the first time? Lol.