The last time I wore a cowboy hat was probably when I was 15 and at Judson School in Arizona (sadly, I just found out Judson closed in 1999 and the property is now yet another unneeded Scottsdale luxury housing development).

Frankly, like most guys who wear glasses, I don't look all that good in a cowboy hat. But if I were in the market for a cowboy hat, I think I'd buy Dylan's "Outlaw Blues" topper.