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Menswear Shops Are On the Upswing in Chicago

The Tie Bar, BOGA, Suit Supply, Bonobos, and more are bringing some great menswear options (and booze) to the city.

Photo: Courtesy of BOGA

If yesterday’s gentleman owned at least one bespoke suit, today’s gentleman doesn’t mind buying off the rack and having it tailored until it looks bespoke. If yesterday’s gentleman owned a fine selection of pocket squares, today’s gentleman takes greater pride in his collection of “statement” socks, his flannel ties, and the single manly candle called Herbal Barbeque or Smoke & Bourbon that burns so brightly on his bathroom counter. So where does this bearded, vaguely entrepreneurial gent do his shopping?

Luckily, the city’s menswear scene has exploded over the past five years, according to Jeffrey Burkard, the CEO of Chicago–based menswear brand BOGA. “[Chicago] men are becoming more confident in stepping outside of their comfort zones,” says Burkard. “They’re learning to up their game and pay attention.”

The new Chicago menswear brands pride themselves on fine fabrics, conscientious production, and a shopping experience that’s more than just sale racks and changing rooms. Take BOGA, who just opened their first brick-and-mortar location at 133 North Jefferson Street. The brand teamed up with John H. Wolf of Wolf Home Design to create a sophisticated space, pairing raw materials with elegant finishes, draping the fitting rooms in denim and calfskin, and finishing off the store with a 65-inch flatscreen TV and a fully stocked bar.

Booze is a common theme in the quest for the sartorial gent’s heart. The Tie Bar—an online shopping site that’s headquartered in Chicago—opens their first pop-up store at 918 West Armitage on October 17, and they’re not called The Tie Bar for nothing. Their VP of Merchandising, Allyson Wicha Lewis, says that the design of the pop-up is focused on “creating a masculine yet warm environment that feels welcoming to guys. They can come in and have a drink with their friends in addition to shopping.”

Like Burkard, Lewis also feels that the Chicago menswear scene is on a serious upswing, crediting “innovative brands like Suit Supply and Bonobos opening stores in the city, as well as Chicago-based startups like The Trunk Club” for turning Chicago into a “destination for men’s fashion.” In addition to store openings, there are a slew of fashionable, male-focused events happening at Haberdash locations all around the city in partnership with GQ, from “How to Improve your Skincare” (October 9-11) to “How to Wear a Filson Briefcase” (October 9-16).

Of course, a successful menswear brand isn’t necessarily the one with the best events or the most Kentucky Bourbon Barrel Ale on tap. All the booze in the world can’t make shopping a painless experience for reluctant guys unless the shopping itself is streamlined. To that end, BOGA focuses intensely on color theory to simplify the process of building a great gentleman’s wardrobe. For example, all of their blues have the same tones, and all of those blues go well with all of their gray tones, and all of their brown shoes match perfectly with their brown belts. Science! The idea, says Burkard, is to make the male shopping experience more intuitive and less frustrating. And sure, a drink can’t hurt.

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