Derby Hat

Winston Classic Wool Derby
Buy It Now at Hats In The Belfry, $24

Chances are, your first instinct for a hat is a top hat. Ignore that instinct, because you want to look classy, not like a magician. The derby is the perfect balance between a formal top hat and a totally douchey fedora, and works well with a variety of faces, not to mention it's been co-signed by stylish guys like T.I. and A-Trak. Just make sure to take it off indoors like a gentleman.