I've never worn a cowboy hat, never found one that fit/look right on me. I wore a baseball cap anytime I left the house from age 18-24ish, then I turned into somewhat of a greaser and started wearing my hair more. Now, I never wear hats indoors therefore I rarely wear one unless I know I won't be going indoors once I leave the house, like on a car cruise or something.
-Robb