On several occasions we've debated the value of hats. You've got your fedora, your bowler, boss of the plains, bucket hat, flat cap, Homburg, etc. And those are just in the men's category.
For posterity I would like to note that James Spader can wear the fuck out of a hat. Not sure how to categorize the one above. Probably a fedora, but the brim is rather sassy. His hat says clearly to everyone paying attention, "I don't give a FUCK. I am the boss of you." And so he is! Although The Blacklist, the show itself, is sort of on the fence.