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18th Street Market Supply Co
Photograph: Jaclyn Rivas 18th Street Market Supply Co

The best vintage clothing stores

Chicago's best vintage clothing stores have everything from '60s cocktail dresses and jazzy tracksuits to fine menswear

By Jess Keys

The best vintage clothing stores in Chicago are made for you to shop until you drop. Sure, shopping at new stores is also great, but unearthing a one-of-a-kind vintage piece just really gets our hearts racing. Whether you're in the market for some new (old?) cowboy boots and can't find any at the shoe stores, want to update your collection of costume jewelry or you're looking for an authentic '70s maxi, you'll want to put these vintage clothing stores on your list before your next party at one of the best nightclubs.

RECOMMENDED: Shop the best clothing stores in Chicago

Best vintage stores

1. Market Supply Co.

Shopping Accessories Lower West Side

Find all the vintage men's and women's clothing your heart desires and more at this hip and thrifty store in Pilsen. Duds range from the early 1900s to 1990s and include everything from dresses and jackets to hats, ties and shoes. You'll definitely be able to tell that owners Karyn Dethrow and Michael Ader travel all across the country to hand-pick the inventory shoppers will love best. 

2. Comet Vintage

Shopping Boutiques Lower West Side

Jen Thomas and Jamie Roelofs don’t waste any time. When the two friends were working at a vintage shop in Pilsen in 2011, they quickly decided they wanted to open their own store. And just a couple of months later, Comet Vintage opened its doors in the neighborhood. The shop specializes in vintage clothing (the dress selection in particular is unparalleled) and housewares from the 1920s through the late ’70s—all at affordable prices ($10–$30) in an expertly organized, posh setting. 


3. Lost Girls Vintage

Shopping Boutiques River West/West Town

This 1976 RV-turned-boutique travels throughout the city with some of the best vintage fashion on board. From kimonos and 1950s dresses for ladies to Western shirts and leather oxfords for guys, the selection offers something for everyone in sizes 00–18. Visit Facebook to find out where the RV (a.k.a. "Winnie") is headed next or visit the new Lost Girls showroom, recently relocated from Pilsen to Bucktown, opening in May 2016.  

4. Dovetail

Shopping Boutiques River West/West Town

This immaculate, uncluttered vintage shop could easily pass for a contemporary boutique, thanks to its carefully chosen, mint-condition men’s and women’s clothing, accessories and ’50s–’80s home decor. On any given day, the ever-rotating selection might include items like white mid-’60s leather ankle boots, vintage cotton maxi dresses, 1970s leather belts and more. 

knee deep vintage, pilsen, vintage shops
Photograph: Jaclyn Rivas

5. Knee Deep Vintage

Shopping Thrift stores Lower West Side

Tired of traveling from Brighton Park to the North Side for cool, thrifty finds, Trent Marinelli and Carlos Lourenco took matters into their own hands by opening this vintage shop in nearby Pilsen in 2008. Just off the Pink Line, the store (in a former meeting space the duo renovated) specializes in fashion-forward vintage clothing and accessories, as well as those harder to find gems from the '20s-'50s. Stop in often to score the best steals. (We once found a mint condition, 1970s Burberry trench here for $90!) 

6. Richard's Fabulous Finds

Shopping Menswear Wicker Park

This quirky Humboldt Park vintage shop has yet to be discovered by the masses, so get there quick. As Chicago's only all-men's vintage shop offering European-inspired menswear, gifts and housewares, it alone is worth the trip to the WOW (West of Western) district. Score silk equestrian print pocket squares, bow ties, plaid blazers, overcoats, hats, vintage luggage, chairs and much more at the North Avenue storefront. If you're in luck, you can get styled by Richard himself—or shop items online through the shop's Etsy and eBay accounts. 

Photo: Michael Maxner

7. Kokorokoko

Shopping Boutiques Wicker Park

This Wicker Park vintage shop is Chicago's go-to for fresh '80s and '90s gear. The bright and funky store stocks clothing for both men and women, from vintage overalls to cartoon button downs, windbreakers, cowboy boots, quirky jewelry and accessories. (Dennis Rodman stickers, anyone?) All resale items are less than $100—it's not hard to find a treasure here, on any budget.

8. Seek Vintage

Shopping Boutiques River West/West Town

In 2010, Chris Hunt quit his job in New York to open this well-curated West Town vintage shop, aiming to "redefine vintage." Well, he succeeded. The merchandise here is high quality and charming, from housewares to clothing and accessories spanning from the 1930s–1980s. You'll find mid-century glassware Don Draper would be jealous of, as well as vintage Pyrex baking dishes. If fashion is more your thing, peruse the racks and racks of '50s–'70s dresses, jackets for men and women, handbags, ties, belts, shoes and denim. You may even find some vintage pajamas!  

Photograph: Andrew Nawrocki

9. Vintage Underground

Shopping Bridal stores Wicker Park

Browsing through the piles of heavy costume jewels at this Wicker Park store feels a lot like rummaging through your grandma’s basement. (And we mean this in the best way possible.) Aside from a jewelry collection that would make Iris Apfel proud, the shop also stocks clothing, handbags, shoes, housewares and home furnishings at a wide range of price points. 

Photograph: Andrew Nawrocki

10. Lulu's on the Avenue

Shopping Womenswear Magnificent Mile

Owner Laurie Davis opened this posh Michigan Avenue vintage dress shop to complement the other high-end stores along the Mag Mile (Lanvin, Burberry, etc). The shops merch also includes an abundance of vintage jewels, hats and handbags. On any given day, you might find a pristine beaded 1920s flapper dress ($475) an LBD from the '90s ($375) or boho 1970s statement necklace ($238). 


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