Neighborhood: Near North Side
Address672 N. Wells St.
Website: leaders1354.com  

Alongside Jugrnaut (427 S. Dearborn St.), Leaders—as the name so poetically implies—is a pioneer in Chicago streetwear. You'll find prevailing labels (read: Billionaire Boys Club, 10.Deep and Jordan) as well as major sneaker releases at this downtown boutique, but the in-house brand (the New Era fitted hats, in particular) deserve a place in your rotation. Also, if you have $10,000 and some wall space, the store showcases incredible paintings by Hebru Brantley. Copping a piece is a good first step in prepping your apartment for a one-night stand, and it's about time you replaced that Derrick Rose Fathead.