INFEASIBLE: Straw cowboy hats
(From Hat Country)
Hats are another sticky topic: some people, yours truly included, can never pass off a hat. And frankly, I haven’t figured out why just yet and instead just work off of intuition. That being said, straw cowboy hats are disasterous and usually shoddy items that invoke images of a sweaty hick rather than John Wayne.
Feasible: Short-rim cadet cap
(Brought to you by TeeShirtsRock.com)
If you’re someone that can pull off a hat, then more than likely a short-rim cap like the one above would work for you. The lesson to be learned here is that, unlike other accessories (e.g. rings, bracelets), hats are not meant to be extravagant.