Slim Sweatpants

Engineered Garments T1 Jacket
Buy It Now at Couverture and The Garbstore,  $395

Timberland 6" Premium Scuff Proof Boot
Buy It Now at Eastbay, $150 

Publish Henrik Pants
Buy It Now at Publish,  $84

Channel 1990s hip-hop cool while still staying relevant by taking the classic uniform of sweats, Timbs, and a bomber jacket and getting the fit right. A trim, not skinny silhouette makes you look great without taking away any of that precious street cred.