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If you choose to... Go to a habadashery and have one properly selected, fitted and mated to a corresponding outfit.
Wearing grampas hat with a Hawaiian shirt looks geezer.
And yes... I wear a 10 gallon Stetson with Gus crease - I play Hill Billy Americana
+1 on the Gus crease. Crucial.
If there is someone in the band with one or more of these things, odds are that they are the bass player
1. is wearing glasses
2. has a beard
3. is wearing a hat
4. is over weight
5. is the dorkiest looking member
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.