Buy It Now at Barneys, $945

A leather jacket is a signifier of a man who knows what's up. They're available in a variety of shapes—from motorcycle jackets to sleek looking bombers, but it's gotta fit right, and it has to reflect your personality. If you've got a rebellious edge, definitely opt for a moto jacket, if you're into looking more classic and put-together, you can't go wrong with a bomber.