I'm considering becoming a hat person with the onslaught of winter weather (well at least in Charleston it's really not winter but it's a bit cooler) and I'm not sure which type of hat I should go for. I would like something classy but a little rock and roll and I fear the fedora may look a little Justin Timberlake. Suggestions?

I'd been looking to do the same look over Winter in Australia, but just could never find a good enough hat. I'd certainly go for the fedora style hat. Those that you see stocked in Europe are perfectly modern, with a much shorter brim than the originals - much funkier, and very, very cool.