These Chicago Stores Cater to Guys With Style

Every woman wants a sharp dressed man (cue the ZZ Top song). But the changing fashions resorting to more relaxed styles means fewer opportunities to find cool boutiques serving up suits and ties.

To be perfectly honest, you can get that look anywhere, so why not go out of your way to discover a few unique pieces to add to your existing wardrobe when you’re traveling to the Windy City? The following Chicago stores cater to men and offer gems worth checking out, whether you’re shopping for yourself or for someone else. They range from the clubby Akira Men to the more upscale Trunk Club.

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BLVDier chicago
Photo courtesy of BLVDier

Clothier fitter Zach Uttich wants to make custom-designed suits more accessible. His stylish, yet understated shop in Fulton Market District opened in 2015 to offer men quality suits, shirts, trousers and more at reasonable prices. For example, BLVDier's half-canvassed suits start at $825 and fully canvassed suits at $895. Clients may also choose from 40 different buttons and 120 different linings alone.

211 N. Green St.

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Century Fashions Big & Tall

Century Fashions chicago
Photo courtesy of Century Fashions

Open 365 days a year, Century Fashions Big & Tall store caters to larger-to-fit sizes with fashionable clothing to make men shine among their slimmer counterparts. The apparel errs mostly on the casual side and much of it can be purchased at a deep discount. It’s a 20-minute drive to the South Side from downtown.

4756 S. Ashland Ave.

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Sir & Madame

Sir & Madame chicago
Photo courtesy of Sir & Madame

This vintage-obsessed shop, located in Wicker Park and owned by a husband-and-wife team, sells enough unique items, guaranteeing you’ll leave with something few people own. The carefully curated collections for men, which include an exceptional Levi’s selection, are detailed oriented, right down to the socks.

938 N. Damen Ave.

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Trunk Club

trunk club box
Photo courtesy of Trunk Club

Ideal for the busy businessman or super-social socialite with expendable dollars, Trunk Club—a Nordstrom Company—takes the personal shopper to the next level. To join, clients can sign up online or visit the Chicago store to create a profile with stats, preferences, etc. After that, a “trunk” shows up to your door on a regular basis, and you pay for the clothes you want and send the rest back. It’s that simple. The perks of visiting the brick and mortar store, which is located one mile from Millennium Park, includes taking advantage of the fully stocked bar. We hear there’s an enviable whiskey selection.

325 W. Ohio St.

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