You could buy your shoes from a chain store that can be found in every other major city in the country, or you could add them to your cart online only to ship them back multiple times until you find the right size. Or you could save yourself the hassle while also supporting local by buying footwear at one of these seven independent shops right here in Chicago. There’s a place here for every style, taste and budget, whether you’re looking for classic Clarks, the latest sneaker drop or even a pair of cowboy boots. Here are our favorite Chicago shoe stores for men.
Alamo Shoes
Andersonville
This Andersonville mainstay, a family business that’s been in the neighborhood since 1973, offers old-school service and contemporary men’s styles from brands such as Merrell, Clarks, Rockport and Born. Experienced, knowledgeable staff will properly measure your feet and guide you to brands that best fit your needs. Competitive prices, a customer parking lot across the street and styles for the whole family make Alamo a citywide favorite.
Alcala’s Western Wear
West Town
A family-owned fixture since 1972, Alcala’s is the go-to spot for cowboy boots in the Windy City. You can spot its massive neon sign — with an accompanying rearing horse — from blocks away of the massive West Town store. Inside, you’ll find more than 8,000 pairs of boots in stock, made from alligator to eel to cowhide in an array of colors and styles. Finish your look off with an authentic Stetson and a charro shirt.
Dashing Chicago
Loop
Much like its location in the Loop’s storied Monadnock Building, Dashing Chicago blends history and style, focusing on heritage luxury shoe brands including Alden and Edward Green. The store puts an emphasis on personalized service that’s high-end without being stuffy, offering custom fittings, as well as shoe restoration and polishing services.
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Wicker Park
This Wicker Park menswear shop owned by George Vlagos is an outgrowth of Oak Street Bootmakers, a line of popular shoes and boots he started that are fully recraftable (meaning the soles and insoles can be replaced repeatedly). That footwear line is sold here, along with other American brands including Battenwear and All We Remember.
Saint Alfred
Wicker Park
Sneaker fiends have been flocking to this Wicker Park shop since it opened in the early 2000s to check out the carefully chosen selection of streetwear styles and collabs with top footwear brands including New Balance, Converse and Asics. Raffles are often held for especially sought-after styles. The owners display their Chicago pride with fashions that highlight Windy City teams and icons, and by hosting local musicians and DJs in store.
Marc Nolan
West Loop
Sebastian Malczewski founded this men’s footwear brand in 2018 — using the first names of his mentor and son — as a direct-to-consumer line. In 2022, he opened a West Loop flagship store featuring his classic sneaker, boot and loafer styles that incorporate fresh details and bold colors. The best part? His stylish looks start at a very wallet-friendly $125.
Notre
West Loop
Known for its highly curated selection of global styles, Notre is one of Chicago’s top spots for luxury streetwear. The West Loop showroom stocks a limited selection of its expansive online offerings, which include men’s footwear styles from household names like Dr. Martens and Adidas to pricier brands like Peter Do and Marsèll. Its owners conceived the space as a hangout spot, art piece and place to bring social change, as the brand often holds fundraisers for local charities here.
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