I've always thought I look stupid in hats.
Me, too--I've always thought I look dorky in hats, and have very rarely owned any in my forty years of life. I did purchase one last year, kind of like a fishing hat (not unlike the hat we see Ennis wearing in the latter part of the film), that I wear on some of my drives to Kerrville. I'm thinking of buying a baseball cap for the upcoming trip to Estes Park, but may go ahead and wear my fishing hat instead.
I just can't picture myself in a cowboy hat, though. I would feel thoroughly out of my element duded up like that (but don't mind seeing them on others!).