Brad Richards, 42, is associate director of student and young alumni programming at the Wharton School at Penn. “I like to think of myself as modern prep. Being raised on the Main Line and going to an Ivy League school, a lot of my style is traditionally preppy,” he says. “But I like to update it and modernize it.” He’s a big fan of building diverse looks around an iconic item, like a pocket square or a good pair of brogues. “The best investment I ever made,” he says, “was a custom suit—it’s personal and traditional but incredibly flexible.”

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