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David Greenleaf

21, marketing and psychology student at Loyola University of Chicago.

Dries Van Noten wool cardigan, $585, at Barneys New York, Chicago. Y’s by Yohji Yamamoto wool linen trousers, $660, and leather and rubber slip-on shoes, $290, at Yohji Yamamoto, New York. Josh Pololl T-shirt, $64, at apartment number 9, Chicago.

Benjamin Firke

16, student at The Latin School of Chicago who just finished writing his first full-length play.

“My grandpa wears the complete line from the J. Peterman catalog.”

” My style: My signature $2 hat.”

Martin Margiela wool cardigan, $433, at apartment number 9, Chicago. Paul Smith striped shirt, $225, at Barneys New York, Chicago. John Varvatos V-neck sweater vest, $350, at Barneys New York, Chicago. Paul Smith tweed plaid trousers, $330, and Lee Allison silk bow tie, $52, at apartment number 9.

Kyle Anderson

19, student at Harold Washington College studying computer science.

“I never got to know my grandfather, but he always had good style in the photos that I saw of him.”

Y’s by Yohji Yamamoto wool/linen tweed hat, $200, at Yohji Yamamoto, New York. Coast cotton shirt, $265, at apartment number 9. Modern Amusement V-neck sweater, $110, at His Stuff, Chicago. Dries Van Noten wool scarf, $150, at Barneys New York, Chicago.

Andrew Vratil

25, chef at Trotter’s To Go and owner of ENO, wood design.

“My grandfather wore his clothes like a uniform. He had his own style, and it worked for him.”

“My style: A combination of prep school, art school and old man.”

Gucci cashmere cardigan, $645, at Neiman Marcus. Chrome Hearts tank, $55, at George Greene, Chicago.

Brad Bolt

23, server at Francesca’s Forno and student at the University of Illinois-Chicago majoring in photography.

“My grandfather tells great dirty jokes.”

Dolce & Gabbana wool double cardigan, $995, at Marshall Field’s and Saks Fifth Avenue. Ribbed tank by Gap. Jil Sander denim pants with plaid lining, $485, at Barneys New York, Chicago. Alain Mikli glasses at Optica, Chicago. Styling by Patric Chauvez, grooming by Rachel Reiman, both Elite, Chicago.