Do you wear a hat while playing?. The right hat on the right person looks great. I personally can’t stand anything on my head, but do sometimes wonder what would be a cool hat to wear. I’ve always liked the look of a bowler hat like Stan Laurel wore, but I’m not going to shell out that kind of dough if I was too embarrassed to wear it. Not to mention it would have to be the right sort of band/gig. My hair’s gone on permanent vacation , so if I’m outdoors in the summer I have no choice but to wear a ball cap to keep from frying.