Bonobos
Chicago-native and Bonobos founder Andy Dunn (he started the brand with Trunk Club’s Brian Spaly) just opened Chicago’s first guideshop, where stylists provide one-on-one consultations with guys to find the perfect-fitting pair of pants and dole out advice on how to wear everything from plaid oxfords to bowties to embroidered cords. While he shops, you can sidle up to the in-store bar for a cocktail and pick out one of the all-American oxfords, perfect for “borrowing” from your guy’s closet.
Bonobos, 313 West Superior Street (between Orleans and Franklin streets); 312-465-2499.

Photo: Courtesy of Bonobos