2. Supreme
Do I really need to say anything here? The only reason Supreme's not #1 is because James Jebbia probably wouldn't want to be included anywhere near a streetwear list. Supreme is a skateboarding and lifestyle brand from New York, and since it's inception in the late '90s, has unequivocally donned the crown of streetwear cool. How? Through classic, core product of the utmost quality, and the most limited distribution you can establish. Not only do they evade wholesale, they sell exclusively within their own name-brand storefronts, and even then it's an uphill battle. It starts with the box-logo tees, then it moves to their high-profile shoe collaborations, and don't get me started on their artist series skate decks (I slept on the Robert Longo collection). It says so much about streetwear that the best streetwear brand in the world isn't actually streetwear at all. And that's Supreme.