A lot of people think of college as a chance to reinvent their style—but not Harry Kagan, who’s 18 and fresh out of Walter Payton College Prep. At freshman orientation at Ithaca College, he says, just his regular street wear was radical enough: “It didn’t seem like anyone really understood my fashion sense. Most of them were from small towns.” When putting together an outfit, Kagan usually starts at the bottom, with a pair Nikes or Vans, which he buys at Saint Alfred in Wicker Park, and goes from there. Here he chose a pair of Nicole Farhi boots—not the kind of thing he normally finds occasion to wear, but “I like cleaning up now and again.” The jeans, from Levi’s Capital E line, are his own and the T-shirt is by Anke Loh; he liked its bright hue and stark graphic. He got his Nooka watch in Paris; it displays the time using bars that stack up according to the hour. His hat is also from Saint Alfred and the glasses are a nod to one of his style icons, Elvis Costello.

Where to buy

Boots, $425, at Guise
T-shirt, $75, at ankeloh.net

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