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I'm more trusting now than I was six years ago."

Another top contender on the minimal front is a low black leather sneaker

EXPERT TIP Christina Santelli is the Owner and Founder of Style Me New, a wardrobe styling concierge based in Tampa, Florida

Previously, Cheatham was a commerce editor for Spy, and he has written for Travel + Leisure

The Fresh Prince of Bel-Air Before the slap that was felt around the world, Will Smith played a character whose East Coast-meets-West Coast look in The Fresh Prince of Bel-Air laid the groundwork for the color blocking, matching track suits and varsity-inspired insignias that are trending right now