For 20 years, Supreme New York has helped promote and define a certain look. Call it downtown casual or something like that if you want, but once you take a few looks through their shop or their Instagram, you'll get the idea.

It's probably too cool for you to pull off, at least right now, but who knows -- start with a pair of their boots, maybe add some sunglasses and a hat, then a jacket. Before you know it, you might start looking pretty badass.