Independence

George Vlagos, the founder and designer director of Oak Street Bootmakers, opened Independence in 2012 with the “desire to build a home for so many made in USA brands that weren’t represented in Chicago.” As its name suggests, the shop is located on Oak Street (47 East to be exact), in a small but meticulously merchandised space above George Greene, tucked away from the city’s nearby department stores and high-end designer boutiques. The space informally serves as the Chicago flagship for Oak Street Bootmakers—offering the entire product line plus exclusives and special events—while also carrying a coveted range of American and Japanese brands, such as Engineered Garments, Kapital, orSlow and Gitman Vintage. And, while many of the store’s offerings are Americana-inspired, Vlagos does not see Independence as a heritage store: “Though classic Americana is at the root of who we are, over the past 6 years, we have loved to explore and carry brands from Japan, the UK, and beyond. Even some of our Made in USA brands would better fit the title of avant-garde, to the heritage,” he clarifies through email.

While the shop’s large wall-mounted American flags, vintage photographs and footballs, steel pipe garment racks and abundance of dark stained wood denotes a connection the past, Independence and the brands it carries are rooted firmly in the present even as they pull from the aesthetics and techniques of bygone eras. A single look at items like Kapital’s beloved multi-functional Ring Coat, Engineered Garments playful yet practical Holster Bag and the natural indigo dyed Haori Western Denim Shirt from Japan Blue’s newest line Soulive solely place Independence in the 21st century where nearly anything can be remixed with anything else to create something surprising and beautiful. And, while the store carries numerous statement pieces, it also stocks superbly made wardrobe staples, such as oxford shirts form Gitman Bros. Vintage and merino wool athletic wear from newcomer Northwestern Knitting Co.

Independence’s range of products reflects its development over the past six years, as well as its diverse customer base: “For many of our customers, Independence is the store where they purchased their first pair of selvedge denim. Years later, while their style may have changed, and often times, become more adventurous, Independence is still their go-to shop,” Vlagos explains. Yet, while the store caters to a variance of shoppers—from fashion savvy Kapital fans to older customers who, according to Vlagos, talk of how they “‘remember when product used to be made this well,’”—the thing that ties them together is the way they are received by Vlagos and his staff. Both Vlagos and shop manager Drew stressed the store’s open door policy and willingness to educate customers without condescension—an approach that feels particularly true to the values of the Midwest. Like Grailed, Vlagos sees Independence as a “meeting place for like-minded individuals to discuss quality product,” and with a keen focus on brands that meld old-world production with new-world design, Independence should continue to thrive as Chicago’s retail epicenter for remixed Americana.

George Greene

George Greene was founded in 2001 by John C. Jones, John Moran and Edmund Paszylk, a trio of highly experienced luxury retail salespeople who met while working at Oak Street’s legendary, but now defunct, boutique, Ultimo (where Jones ran the men’s business for 27 years). After Ultimo changed ownership in 2000, the three left to open their own shop, whose name they chose for its British appearance and as a subtle reference to Jones’s terrier. For the past eighteen years, George Greene has reinterpreted Ultimo’s tradition of mixing tailoring with streetwear, thereby establishing itself as one of the preeminent Midwest shopping destinations for menswear enthusiasts: “The first difference is George Greene is not streetwear. We are not RSVP Gallery, but at the same time we are not a stuck-up store. We are a fashion luxury store and that’s what’s kind of missing everywhere. You have the department stores that have the good and the bad, but there’s no filter. Or you have the streetwear stores or you have luxury suiting stores. We are a mix of all of that, which is what makes us special and different,” Jaime, George Green’s merchandiser and assistant buyer, explains.

Located on the ground floor of 49 E Oak Street (right below Independence) in a three-room space, George Greene is filled to the brim with chrome garment racks and glass shelves and display cases. The fact that the interior of the shop is not decorated with the same “curated” zeal of so many of today’s Instagram-ready high-end menswear boutiques is a charming reminder to the days of when a store’s décor and brand list reflected the taste of its owner instead of a strategic plan to coax in-store customers as physical retail spaces have struggled to survive the increasingly competitive global fashion market. And, despite its humble space, George Greene presents an impressive and wide-ranging brand list—from Yohji Yamamoto to Thom Browne to Chrome Hearts to Off-White to Kiton—that is comparable to that of luxury department stores such as Barney’s with ten times the space and budget.

Most impressively, George Greene has managed to thrive in a business that is increasingly shifting online despite not having a web shop. Even though the store will be reimaging its website in the coming months—with plans to feature seasonal editorials of the merchandise, alongside updated information that directly connects to the shop’s social media—there are no current plans to introduce a fully-fledged webstore. Instead, George Greene drives customers in-store with a combination of rare and hyped merchandise and superior service. The shop is the only place to buy Chrome Hearts in the Midwest and boasts a jaw-dropping collection from the brand that includes sterling silver rings, pendants, pens, eyewear and even a highly ornate silver-studded leather rider’s jacket. Other standouts during a recent visit include beautifully marled sweaters from knitwear brand Inis Meáin and a painted Yohji Yamamoto Pour Homme sport coat from the designer’s Spring/Summer 2018 runway show that bridges the gap between fashion and fine art. Plus, with a staff of master tailors to meet a range of customer needs—including free alterations on full-priced clothing, alterations on returning clients’ wardrobes and made-to-measure suiting—it’s easy to see why George Greene is worth returning to again and again.

Boneyard Chicago

Boneyard Chicago began as online vintage shop over three years ago and moved into its physical retail space at 917 N. Ashland Avenue in 2016. The owners, Tony and Jacob, met selling vintage gear and came to respect each other’s hustle; they were eventually given the opportunity to liquidate the stock of a 30 year old mom-and-pop sneaker store they’d bought from for years, which allowed them to accrue the capital to start Boneyard—the name Tony’s dad used for junkyards when Tony was a kid. But nostalgia didn’t merely inspire Boneyard’s name—it proliferates nearly every aspect of the shop. From the white sneaker wall with movable plastic shelves, to the life-sized Michael Jordan and Shaquille O'Neal cardboard cutouts, to the vintage Champion, The North Face and Columbia apparel arranged on clothing racks, and even down to its in-house apparel and accessories—Boneyard is all about celebrating the old, archival and nostalgic. This applies to Boneyard’s own logo as well, which takes its skull and silverware design from “Eat the Rich” T-shirts Jacob bought years ago.

Yet, Boneyard is far from your average vintage or consignment store: “We’re very curated. We won’t just sell any kind of vintage. We buy strictly things that we like,” Jacob explains. And, although Jacob, Tony, and store manager Griff may not drape themselves in the latest Supreme drops, their collective taste level creates a unique space that place some of the most hyped street and sportswear brands of the present—such as Supreme, Bape, Yeezy, Nike, and adidas—alongside vintage pieces that inspire so many of those brands’ designs. While it might feel disconcerting for some to see a Supreme toy blimp hanging against the backdrop of vintage Chicago Bulls tees, it makes complete sense when you consider that Supreme recently dropped jackets, jerseys, shorts and Air Force 1s in collaboration with Nike and the NBA.

While Jacob, Tony and Griff have increasingly decided to cater to the tastes of their customers—“This is what our customers are wearing. This is what we should offer in store,” Jacob explains—it’s clear that Boneyard resonates with Chicagoans far beyond hype. “What people dig about our shop is that we’re true to ourselves. Our best-selling item is our store merchandise,” Jacob continues. So, while Boneyard may be the go-to spot in Chicago to buy or sell the most recent hyped release, don’t be surprised if it focuses more and more on in-house apparel inspired by the things that have influenced its owners. “We try to drop new merchandise all the time inspired by things we love, Jacob explains. “We do have some collaborations on the horizon, collaborations with people we’re fans of.”

Saint Alfred

Founded in 2005 by the owners of influential Hawaiian sneaker boutique KICKS/HI, Saint Alfred has been a can’t miss destination for Midwest sneakerheads for the past thirteen years. The founders decided to open the shop in Chicago because of how many sneakers they were shipping to the city. One of the first boutiques to open in the city’s now trendy Wicker Park neighborhood (at 1531 N. Milwaukee Ave.), Saint Alfred has helped popularize streetwear and sneaker culture in Chicago over the past decade. The store is currently run by general manager Frank DiGiovanni, brand manager Joe Shaefer and store manager, buyer and photographer David Robinson. Robinson was introduced to the shop by a friend 10 years ago and has seen how both Saint Alfred and Wicker Park have changed over that time span. “When we first opened, it was 80-90 percent footwear and the rest was clothing. At this point it might be 50-50,” he explains. So, while the boutique boasts a Tier Zero account for Nike, along with Consortium and Originals accounts for adidas, it also has bragging rights as being the first shop in Chicago to carry WTAPS, Neighborhood, Visvim and Undercover’s men’s line.

The store’s 50-50 split between sneakers and high-end streetwear is immediately evident as you enter the space. A large industrial metal pipe (that also serves as seating) connected to a clothing rack filled mainly with the shop’s in-house apparel (tees, hoodies and collaborative caps with Ebbets Field Flannels) divides the store: on the left side are 10 jam-packed shelves of men’s and women’s sneakers from Nike, adidas, Jordan Brand, New Balance, Converse, Asics, Vans and many more; on the right side there are five wall-mounted racks filled with apparel from some of the most relevant streetwear brands of the past 25 years. This roster includes Undercover, Neighborhood, Visvim and Stüssy alongside newer brands—like Brain Dead and Cav Empt—that have already made waves. Built-in glass cases in the store’s front counter and along its walls serve to showcase some of Saint Alfred’s priciest pieces, such as footwear from Visvim, as well as ephemera and accessories from names like Neighborhood.

While Saint Alfred’s merchandising can initially give off a vibe that it’s ‘okay to look, but not to touch,’ that sentiment couldn’t be further from the store’s ethos. “A few things we’re big on: Customer service, providing a welcoming chill atmosphere, whether you’re a sneakerhead or someone who walks by and comes in because you’re curious,” Robinson explains. “We’re not a museum. You can touch it. You don’t have to buy it. You don’t have to ever buy it,” he continues. Saint Alfred may be a go-to spot for hyped brands and limited sneaker releases, but Robinson and the rest of the store’s staff approach their jobs with humility. Robinson names “timelessness and quality” as the two pillars of the store and dismisses the idea that hype defines the importance of a product. “We treat all product equal. We treat an in-line Sk8-Hi the same way as an Off-White Blazer.” More than any product, Robinson and the team at Saint Alfred seem interested in representing Chicago; the store’s in-house apparel often references the city, including a recent line of Champion Reverse Weave tees, sweatshirts and hoodies emblazoned with its 773 area code. While Saint Alfred may rep its hometown hard, the store’s reach goes far beyond the city limits. “We have a really small team. There’s no big money behind us,” Robinson clarifies. “For such a small team to resonate countrywide and even globally is amazing in and of itself.”

RSVP Gallery

Although we weren’t able to connect with the creative team behind RSVP Gallery, any Chicago shop guide would be remiss without including the highly influential store. Opened in 2009 in at 1753 N. Damen Ave. in Wicker Park by Just Don creator Don C, Off-White designer Virgil Abloh and photographer Marc Moran, RSVP Gallery (the abbreviation for “répondez s’il vous plaît” or “please respond”) has helped usher in the modern age of boutiques-as-galleries. The shop is located in an underground space that, if not for a few small street-level windows, would be completely detached from the world above. The shop’s brick walls, neon lights and designer logos, Murakami plush toys, Just Don python basketballs and glass cases filled with oversized action figures make it feel like a streetwear fanatic’s dream bedroom.

With a brand list that features a murderer’s row of today’s most hyped designers—including Faith Connexion, Fear of God, Raf Simons, Stone Island, Undercover, Yeezy and so many more—it’s plain to see why RSVP is a required destination for fashion savvy Chicagoans and tourists alike. Although the shop sells merchandise that, at times, matches the price point of fine art, the staff doesn’t act like a fussy group of curators, instead allowing customers room to breathe and take in all of the grails.

While RSVP Gallery does deal in the currency of hype, Don C, Abloh and Moran also have an eye for up-and-coming designers, such as Yuta Hosokowa’s brand Readymade, which hand-crafts U.S. military items into high-end garments and accessories—including a 2016 capsule collection with Just Don. Celebrity connections aside, it is the founders’ collective eyes for the new that makes the shop a worthy destination, whether or not you have a few thousand dollars to spend.