Welcome to the Windy City: Get to Know the Sneaker Stores That Run Chicago

Where do sneakerheads go in Chi-town?

photos by Vince Sirico

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by Jennifer Ernst Beaudry

The City with Big Shoulders is the third-largest in the U.S. (trailing only New York City and LA). It’s known for deep-dish pizza; Buddy Guy and the blues; native sons Kanye West and Common. And, of course, it’s known for being the home court of Michael Jordan, the GOAT, whose soaring silhouette sold more than $2 billion worth of products last year, more than a decade after retiring.

But even that rich legacy isn’t enough to shake a longstanding feeling that Chicago never gets its due, at least as a sneaker city.

“The thing with Chicago,” said David Rasool Robinson, manager of the city’s legendary Saint Alfred boutique. “We always have been looked over.” 

But there are signs that Chicago is shaking off its Second City reputation when it comes to kicks. Today, established local legends are crafting national — and international — profiles with new launches and collaborations, and an influx of newer shops are bringing fresh brands and their own perspective to sneaker culture.

“Chicago has it’s own style — it takes cues from a variety of other places but it makes it it’s own,” Robinson said. “And in the past few years, more of the world is looking to cues from Chicago and taking influence from us.” 

"More of the world is looking to cues from Chicago and taking influence from us.” 

And that is something that founder of Chicago-based Modern Notoriety Oscar Castillo says, is helping to build an even stronger sneaker culture that’s ready to hold its own.

“Chicago’s sneaker scene is one of the most influential in my opinion,” he said. “From the Air Jordan series to Kanye West, everyone owns a piece of Chicago.”

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But there’s more to the Chicago sneaker scene than just where Michael Jordan spent most of his career. RSVP Gallery, the retail space opened in 2009 and run by Don C. and Virgil Abloh (better known as management and creative director to Kanye, respectively), marries a high-end sensibility (Givenchy, 3.1 Phillip Lim, Balmain) to streetwear, with the ultraluxe Just Don snapbacks, Hood By Air apparel and adidas’ Rick Owens and Raf Simons collabs. Don C. also dropped his second sneaker collab with the Jordan Brand earlier this year.

“Kids nowadays, the youth, it’s more fashion-forward — when I was that age it wasn’t about Raf Simons x Adidas, or Common Projects,” Isimeme “Easy” Otabor of RSVP Gallery said. “But Jordans are always going to be big in Chicago.” 

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City stalwart Saint Alfred celebrates its 10th anniversary in August, and in its decade in the city’s Wicker Park neighborhood, the shop made a name for itself as the Windy City’s go-to by being the first to bring in fresh brands to the Chicagoland area at a mix of prices. 

Robinson credits the shop’s “unapologetic” of mixing of styles and brands like Acronym, Carhartt WIP, 10C as well as New Balance, Diadora, Saucony, Jordan and Vans.

 “We have $20 tees mixed with $200 tees,” Robinson, who’s worked at the shop for the past 7 years, said. “We never wanted to price anybody out, and we wanted to bring in brands that maybe people have only been able to see online.” 

Antonio Taylor, the store manager at the city’s Leaders boutique, agrees. The retailer, founded in the city’s Hyde Park neighborhood in 2002 and now located in the upscale Gold Coast area, makes sure it stocks a variety of labels including Pony (with whom the retailer collaborated on a release in January). “We always want to stay true to our name — having things first, but not being trendy all the time,” he said. 

“Chicago in general is still fighting to earn some respect in the fashion world.”

You would think the shops would be extremely competitive in the Chicago market, but it’s actually a lot more cordial than you think. Otabor and others say new openings — and a tight-knit community that supports new players — are bringing new excitement to the city.

Boutique Meyvn opened in May 2014 in Logan Square with Feit, Common Projects, Wose, Patrik Ervell, Needles and Etiquette Clothiers on shelves. Last November, Notre — a men’s streetwear and boutique — opened in the city’s Northside Andersonville neighborhood.

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“We sought out to build a space where everyone was going to feel welcome to come through, chill and shop” said Michael Jaworowski (who owns the store along with Jose Villanueva and AJ Nordstrom). Jaworowski said the store is adding brands including Gosha Rubchinskiy, Hender Scheme, Visvim and the Adidas Kanye West product for fall. 

Internet sales, he said, is the “safety net” that lets him bring in brands like Viberg: “I like it because we can take chances on stuff that the Chicago guy hasn’t seen before.” 

The city’s reputation as Midwestern and safe is bound to change, Jaworowski said: “I think Chicago in general is still fighting to earn some respect in the fashion world, but I think we’re getting there.”

Saint Alfred’s Robinson said that even if the coasts have critical mass on shoppers chasing the edge, people shouldn’t count Chicago out. “It’s a smaller group, or a more niche group, but I would say this: there are people who are more open and more receptive to taking cues and fashion risks.”

And there are enough of those customers, stores say, that it’s definitely not a case of increased competition. “Sometimes I feel like there aren’t enough stores,” Otabor said. “So we all come together, we’re building and helping Chicago in the best way possible.”

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Jaworowski said Notre’s been embraced since opening, with referrals and visits from other owners and no one running interference on brands, like the adidas-Kanye collab that stores like RSVP Gallery could easily have made exclusives.

“It doesn't feel like we're really competing with each other — we're constantly preaching to guys about Saint Alfred and RSVP, and we've heard a lot of love back,” he said. “It's really encouraging to know I can communicate with the other shop owners to get their opinions and to bounce ideas off of and even collaborate on some crazy events in the future that can continue to grow the Chicago customers knowledge of the brands and creators.”

Robinson agreed. “More stores are adding more diversity and depth to the city. The scene is honestly not as strong as I would like it to be — but it’s stronger than it has been,” he said. “We try to add more community and I’m a firm believer that the pie is big enough for everyone.”

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But the shops have bigger ambitions than just growing the local scene.

Through collaborations with brands like New Balance, several with ASICS, and Converse — Saint Alfred has been able to bring their view of Chicago to the world. An ASICS Gel-Lyte III collaboration in 2013 took inspiration from the shores of Lake Michigan, and an upcoming collaboration with a brand Robinson won’t reveal reflects the city’s world-renowned architecture.

“We’re all students of the city, and we take a lot of inspiration from the city,” he said. “We’ve gone from a very niche Chicago boutique to a worldwide footprint, and that’s partially because of us, but it’s an even bigger testament that people are looking.”

And Leaders is taking the mission to bring Chicago to the world literally. The retailer’s second location — and first outside Chicago — is opening in Englewood, N.J.

“Expansion has always been something we talked about — we want to be world known,” Taylor said.

In addition to a Chicago-native store manager, Leaders in New Jersey will be bringing the brand’s eponymous street wear label — with its shoutouts to Hyde Park, “Chicago’s Finest” tagline and graphics that reflect the city.

“So we’re bringing a Chicago perspective,” he said. “The East Coast has certain influences and so does the West Coast; in the middle, we just do us.”