Pulling off a leather jacket the right way takes a studied but not self-conscious combination of style and swagger. Find an icon to emulate. We recommend starting your search with these guys. They did it right.

John Lennon: When the Beatles played Hamburg in the early sixties, they popped amphetamines, played all-night sets, got into fistfights, and rocked badass leather jackets. Take a queue from John (top) and try pairing a dark bomber with a black T-shirt. The mischievous grin? You can't buy that.

Springsteen

Bruce Springsteen: Before he became the Boss, Bruce Springsteen was just a skinny kid from New Jersey with a penchant for patchy beards and leather duds. As though he didn’t look cool enough, the young E Street front man always took care to accessorize his jacket. A chunky knit cap and a leather jacket might not be likely bedfellows, but it works on Bruce. (And here's how to grow and maintain awesome facial hair.)

Peter Fonda

Peter Fonda: 'Easy Rider' was shot on a tight budget, but for writer-director Peter Fonda, the tightest thing on set may have been his close-fitting motocross jacket. Festooned with racing stripes on the front and old glory on the back, it has since become almost as iconic as the film itself. Beginners should leave wearing the stars and bars to people like Captain America, but all the same, consider shooting for a slightly more ostentatious look.