When deciding what to try hat-wise, I'd suggest looking to sartorial inspirations. Who makes you want to wear a hat? Bogart? Indy? Chaplain? Depp? That'll give you a steer from the off. Also, what's your look? Little point, in my minds, in buying a brown fedora if you only ever wear black leather jackets and black denim. When you first start wearing it, don't give up too quickly if it feels odd. Give it time to get used to it. And - limits of work dress codes aside - don't care what anyone else says. In reality, if you're going to stand out from the norm, you don't go around being thin-skinned. Idiots will be idiots. In my experience, the vast majority of people actually mean well, and if they call you "cowboy" in a fedora, or "Al Capone" that's simply their field of reference via popular culture.