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[title]Trunk Club
Some guys are natural-born shoppers, with an instinct for what matches and an appreciation for hitting five stores to find it. Others need Trunk Club. The smart, “why didn’t we think of that?” program has stylists who consult—in person or on Skype—with a male client to assess his taste, needs and lifestyle, and teach him how to mix and match. He’ll receive a box of moderately priced clothes to try on (pants and jeans starting at $90 and button-ups starting at $80), select what suits him and send back the rest. Piece of cake, right? 325 W Ohio St (866-406-2235).—Jessica Herman
Other nominees CakeStyle, Eric Himel, Julie Watson Style, NAC for Style