Con-fident Market

If you've dabbled in Converse All-Stars or Nike Roshe Runs, Sneaker Con Cleveland March 26 is the place to level up your kicks cred. The traveling convention is a sole collector's dream, with vendors selling rare releases and a trading pit for people looking to unload. But if phrases such as colorway (a shoe's themed color combo) make your eyes glaze over and Yeezy Boost sounds like an energy supplement, Omar Madhun, owner of online sneaker and fashion reseller Ship to CLE, has a few tips.

Home court:  While a pair of nostalgic Air Jordans may be tempting, Madhun suggests looking closer to home: Nike ID Kyrie 1s. The Cleveland Cavaliers guard's first signature shoe is highly regarded among collectors, and the Nike ID editions — individually customized online — offer a chance at a one-of-a-kind version. "The day before they took off the Kyrie 1, I went on Nike ID and made eight pairs," says Madhun.

Boxed out:  Shoe values fluctuate like baseball cards or stocks, so protect your investment. Madhun says having an original box — the side label should match the size, style and color — keeps them safe and demonstrates authenticity. "It means the shoes are original," he says. "They didn't just get them from some random dude on the street."