Once I went to a baseball game and I wore a pink shirt that I bought at a gas station on the way there, it had bright blue flowers and robins on it. Nothing about that shirt was cool. It was also too small. I recently came across a picture of me in that shirt. Bad haircut. Dumb sunglasses. Too-small ugly shirt. I think the guys with me was embarrassed. It never occurred to me to be embarrassed.
These days I go mostly with black—black t-shirts, black jeans, black coat. I'm not any cooler than the doofus in the dumb shirt and I don't give more of a shit about how I look, but this what's working now.