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The Stylist

Maybe it's the architecture. Maybe it's the theatre. Maybe it's the jazz, the food, or the art. Whatever the reason, this has always been a gathering point for the sophisticated, fashionable, and urbane. As such, the nest shopping areas in Chicago leave nothing to be desired - expect maybe a few extra arms for carrying home your treasures.

Kyle Hocking

Kyle Hocking is a Chicago-based writer behind The Simple Child, a lifestyle blog covering street-style, travel, fitness and everything in between. The Simple Child was created to fill a gap in men's style coverage - tips for the casual guy. His notes on style & travel are meant to inspire and help keep it simple.

Bonobos

Brick-&-mortar branch of the online retailer, featuring stylish menswear & in-store fittings.

Una Mae’s

Rustic-hip boutique for new & vintage men's & women's clothing, plus personal items & accessories.

SUITSUPPLY

Men's and Women's - Find your own perfect fitting suit. Suits, shoes, tailoring, fitting. Ranked "#1 suit" by Wall Street Journal.

Saint Alfred

Specializing in providing the best streetwear and footwear from around the world.

Independence Chicago

Upscale clothing shop features a hip selection of American-made designer fashions & accessories for men.

Cowboys and Astronauts

Welcome to Cowboys and Astronauts, a men's lifestyle and supplies shop where everyone who clicks or walks through our door—no matter what age, gender, size, or way of life—should feel welcome, excited, and inspired