Cool hats + togs go together like peanut butter and jelly IMHO.
And there's something to be said about the old school hat shops. They're very hard to find these days (nearest one for me is a 2 hr drive), but worth the trip. They have all kinds of styles and can help you find a hat that will look great on your big ole block head. Ordering a quality hat over the internet is a crap shoot, unless you know exactly what you want and what your actual fitted size is.
I always wanted a fedora, but they just look stupid on me.