Borsalino 5

If you're a mobster, circa 1920 to 1960, this is the only hat to have. Sometimes mistakenly called a fedora, it is broader brimmed, broader ribboned, and blocked with a subtle difference.

Looks pretty cool, but it definately requires the suit to go with it (or at least suit pants with suspenders over a wife beater shirt a la Jean Paul Belmondo.) Wearing it with jeans just doesn't cut it.