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 itâ€”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.