27. Tom Waits
Band: Tom Waits
Tom Waits looks and sounds like the devil in human form. We mean that in a good way. His style paid homage to a variety of musical subcultures, mixing Beatnik, Bohemian, and jazz styles into his personal wardrobe. Much like his music, it was familiar but you couldn't quite put your finger on it—but you knew it was good. His headwear always looked good, whether it was the porkpie hats he was known for or the cabbie-style hats he subbed in every so often.