24. Elvis Costello
Band: Elvis Costello and the Attractions
Along with David Byrne and a few others, Elvis Costello was at the forefront of the New Wave movement that developed alongside punk music. With his throwback Buddy Holly-esque glasses, skinny sportcoats, and various porkpie hats and fedoras, Costello quickly set the New Wave sartorial standard that was somewhere between prep's second wave and punk's subversive sensibility. He is the OG hipster, back when the phrase was synonymous with cool and had nothing to do with kale.