The only rules that really matter are these: what a man can do and what a man can't do.

Johnny Depp

After almost a quarter century in front of the camera, Johnny Depp has shown us everything but himself. Not an easy task when you’ve got those cheekbones, that tousled hair, and an unmitigated youthfulness, which Depp has worked hard to cloak by playing reclusive savants and rock ’n’ roll pirates. But we keep searching, trying to nail down his hobo chic—a style that derives from a life spent kicking around the dusty South and the French countryside. “I don’t think he’s remotely interested in fashion. He’s a complete instigator of fashion,” says Penny Rose, the costume designer who collaborated with the actor to create Pirates of the Caribbean’s randy Jack Sparrow. “His look is always eye-stopping, clever, and completely individual.” Or, like the last two drags on one of his hand-rolled cigarettes, raw and unapologetically gratifying.

• A tweak here and there can elevate even the simplest outfits. Notice the rolled-up sleeves, the neckpiece, the beat-up boots instead of sneakers. Small moves like these separate you from the pack.