I think the red hat thing is neat. I wouldn't even interpret it as uniqueness, it's really just a celebration of aging, which isn't going to get much celebration otherwise so ... so it is counter-cultural more than individualistic I would think (yes which is preferable anyway!).
Yea if your young and basically healthy almost anything is going to look good on you, so play about that temporary kindness of nature to get all your clothes from whatever, the city dump maybe, but eventually you'll want to look as good as you can and not be 19 (and sometimes even respectable etc.), and that will take a bit more careful shopping.