Like a Rolling Stone

Bob Dylan

Remember young Guthrie-ite Dylan, the one with the beatnik blue jeans, denim shirt, and corduroy driving hat? Or how about the powder-faced imp headlining The Last Waltz under a floppy pimp lid? Through the decades, Bob Dylan has always tapped into the fashions of the times. “He’s a rotating type,” says documentarian D. A. Pennebaker, who made 1967’s Don’t Look Back. “It never works to try to pin him down.” There was also Biker Bob (see Highway 61 Revisited), who said, “I’ve had black leather jackets since I was 5 years old.” And then there was his other favorite accoutrement—those jet-black shades: “You buy them off the rack, if they fit, and you put them on.” The point is, Dylan’s ever changing style was one of discovery. “There was an air of expectancy. He was there to find out what was going on. And his choice of clothes relates to that,” says Pennebaker. “He was trying to figure out who he was.” He was all those things, and none of them.

• Ray-Ban Wayfarers will always be in style. The look worked for Dylan and Ali, it worked for Cruise, and it’s working now for every band on the planet and every fashion-minded guy in town.