Originally Posted by Jokerman
Honestly I think men with shaved heads look better with a straw type hat. I think baseball caps just look blah.
It's just very hard to make the average baseball cap look stylish since most people who wear them look like Old Navy clad slobs. Being honest, I like the way a backwards baseball hat frames my face and I get lots of good looks when I do it, its just not a style I really want to impress on people. Especially since its hard not to look like Fred Durst.
If you must, I'd say high quality, 100% wool is a must. Top of the World was doing some gray flannel throwback hats a few years ago that were pretty sharp. Unless its vintage I'd stear clear of sports team logo hats.
Black Cherry is one of the few people here I have seen properly rock a baseball cap.