South Loop stores
Each time this local menswear shop opens a new outpost, it seems to outdo itself. The River North location features hot lather shaves in the back of the shop, and this South Loop spot takes that feature and adds a barista-staffed lounge that features La Colombe coffee. Of course, the real reason men flock here is for the well-edited collection of clothing that includes items from Barbour, Gitman Vintage, Baldwin Denim and Haberdash Bespoke no.607, the in-house affordable line of made-to-order canvas suits.
This Midwest-born urban boutique brings stylish street wear to the South Loop. Expect to find plenty of hip-hop and skater gear, as well as vintage apparel. Shop here for the store's namesake label, featuring men's shirts, hoodies, tees and beanies, plus other brands like Mishka, 10 Deep and Billionaire Boys Club.
A knitter's paradise, Loopy Yarns draws yarn fanatics from all over the city. You won't just find the most extensive yarn selection in Chicago, you'll also walk out with some major tips and tricks from its savvy staff, who offer an extensive series of workshops for all skill levels. You'll be knitting enough socks to start up an Etsy side hustle in no time.
Open since 1971, On the Route has expanded from its original Lakeview shop to two additional locations in Chicago. Brands available include Trek, Cannondale, Electra, Bianchi and more. Given that one of the owners is a female cyclist, On the Route stocks the shop with plenty of female-specific cycling gear. Stop in for tune-ups, accessory installation and more.
A family-owned establishment and sister shop to Little Italy's Gentile's, Printers Row Wine Shop is known for its rustic charm and selection of small-batch spirits, craft brews and wine from local distributors. As any good South Loop wino knows, it's the place to be on Friday night, when it offers free wine tastings from 5–8pm. Or, you could join the shop's wine club ($39.99 per month), and pick up a new, hand-picked bottle of red and white to try on the 15th of each month.