Kids can be pretty judgmental on the playground, so I'm not sure it's as simple as "adults judge, kids do not." Some people just naturally express their creativity through their clothing. I think if you used to have fun with your clothes you can certainly get that back. I'm not a particularly creative dresser, so I'm afraid I don't have any good tips for you. I'm hoping some of our more fearless YLFers will chime in!
(And you know, even though I am not a "fearless" dresser, I AM having fun. I thoroughly enjoyed putting together a slightly unconventional cocktail party outfit a couple weeks back...it certainly wasn't avant garde or designed to shock, so the degree of "fearlessness" needed to wear it was pretty low, but I did have fun.)
Thank you for an interesting read!