25. Ian Bradley
Have you ever looked at someone and just straight-up felt depressed because you would never be that cool? Yeah, that's what happens when you look at Ian Bradley. The stuff he wears just looks so dope on him. He's mastered layering and wears a few easy pieces so, so well. Not bad for a guy who isn't a professional model, what he does do though, is style for clients like Uniqlo, Vice Magazine, and The Fader. Sometimes you can find him running the door at The Standard too, so it's obvious he can tell who's really got their style game on lock. Roll up in bootcut jeans and square-toed shoes? Not a chance in hell, bud.