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.

  • 01 of 08
    ••• Photo courtesy of Akira Men

    Targeting a flashy, fashion forward sort of fella, Akira Men showcases edgy shirts, slacks, shoes and accessories. Many of the items may be best described as “conversation starters,” with bold colors, designs and trendy features such as grommets on hats and shoes. Both locations--in Bucktown and Andersonville--boast clubby atmospheres with loud hip-hop, pop and rock music blaring throughout the spaces. Hours: 11 a.m.-9 p.m. Monday through Saturday; 11 a.m.-7 p.m. Sunday. 1910 W. North Ave., 312-423-6693 or 5229 N. Clark St., 773-275-3664

  • 02 of 08
    ••• 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., 630-200-8583

  • 03 of 08
    ••• Photo courtesy of Brooklyn Industries

    With so many similarities between Wicker Park and Brooklyn, it comes as no surprise the only Brooklyn Industries’ Midwest store is located in this hip, near west side neighborhood. It appeals to younger guys for street styles ranging from graphic tees to slouchy, slimmer-cut shorts and slacks. Guys can also find a lot of retro looks in accessories: hats, shoes and bags, to name a few. Hours: 11 a.m.-8 p.m. Monday through Saturday; noon-7 p.m. Sunday. 1426 N. Milwaukee Ave., 773-360-8182

  • 04 of 08
    ••• Photo courtesy of Century Fashions

    Open 365 days a year, the store caters to larger-to-fit sizes with fashionable clothing to make them shine among their slimmer counterparts. The apparel errs mostly on the casual side and much of it can be purchased at deep discount. It’s a 20-minute drive to the South Side from downtown. Hours: 10 a.m.-6:30 p.m. Monday through Friday; 9:30 a.m.-6:30 p.m. Saturday; 9:30 a.m.-5:30 p.m. Sunday. 4756 S. Ashland Ave., 773-247-2100

    Continue to 5 of 8 below.
  • 05 of 08
    ••• Photo courtesy of Mankind

    There's some fresh blood in Wicker Park with the arrival of this men's only shop from the owner of The Silver Room. The space offers a no-frills vibe, yet the clothing has been carefully curated to reflect fresh European looks from Denmark, Germany, France, United Kingdom, Netherlands and Sweden. Hours: noon-8 p.m. Monday through Saturday; 11 a.m.-6 p.m. Sunday 1410 N. Milwaukee Ave., 773-270-2025


  • 06 of 08
    ••• Photo courtesy of Meyvn

    Men who love looking and smelling great, yet insist they're not dandies, are certain to appreciate this fashionable boutique that's on the same block at Longman & Eagle Inn in Logan Square. Meyvn showcases awesome men's designer clothing, accessories and apothecary goods. Deejays spin on weekends. Hours: 10 a.m.-8 p.m. Monday through Friday; 11 a.m.-8 p.m. Saturday; 11 a.m.-5 p.m. Sunday 2627 N. Kedzie Ave., 312-852-6012

  • 07 of 08
    ••• Photo courtesy of Sir & Madame

    The vintage-obsessed shop 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. Hours: 11 a.m.-7 p.m. Monday through Saturday; 11 a.m.-5 p.m. Sunday. 938 N. Damen Ave., 773-489-6660

  • 08 of 08
    ••• Photo courtesy of Trunk Club
    Ideal for the busy businessman or super-social socialite with expendable dollars, Trunk Club 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 store include taking advantage of the fully stocked bar. We hear there’s an enviable whiskey selection. Hours: Vary by appointment. 325 W. Ohio St., 312-266-8700