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  2. Photograph: Martha Williams
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  5. Photograph: Martha Williams
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  23. Photograph: Martha Williams

Chicago Avenue vintage

Find fashions from the '50s and '60s, or go back to the future with '80s and '90s gear, on Chicago and Ashland Avenues.


Very Best Vintage
Head to the designer rack, filled with ’70s and ’80s clothes from designers like Oscar de la Renta, Armani, Yves Saint Laurent and Gucci. The rack also includes a few newer offerings such as a 1980s Coogi skirt, plus ’50s and early ’60s gems such as a primary-colored French-tailored dress and a two-piece suit made by the same designer who tailored some of Marilyn Monroe’s outfits. While designer-rack prices usually range from $60 to $120, the majority of the store’s dresses ring in well below that, including an early-’50s sea-green back-tie apron dress ($38) and a mid-’50s strapless peacock-patterned sarong dress ($68). 1919 W Chicago Ave (312-226-5530).

The ’80s and early-’90s wear in this shop will invoke either wistful nostalgia or shiver-inducing flashbacks (animal-print Zubaz, anyone?). Ross Kelly, a former buyer for a streetwear company, owns the shop with Sasha Hodges, a photo stylist. He describes the styles in terms of TV characters from the era: “These Dwayne Wayne [A Different World] flip-up sunglasses [$28, others $18–$100] are really big right now,” he says. So are bright, androgynous-cut button-downs that take a cue from Mayim Bialik’s Blossom. Less-risky selections include a form-fitting late-’80s black-and-purple button dress ($64), a hot pink- and purple-striped cropped jacket ($38) and Candie’s-style ankle boots ($52). Kelly sees the looks gaining a wider audience: “Nineties stuff is popping up everywhere,” he says. “Look at Marc Jacobs: He just did some Z Cavaricci copies.” 1112 N Ashland Ave (773-252-6996).

Seek Vintage
Stylish BFFs Chris Hunt and Audra Yeomans quit their jobs in New York to open this well-curated shop in April. Find midcentury glass- and dishware and ’50s–’70s dresses and tops, plus ties and belts—including an ’80s blue leather crisscross number ($12). Shoes, such as a Greek-made blue-and-white leather pair from the ’70s ($18), and flattering cuts such as a ’50s tropical-print dress ($45), are also draws. The partners recently started a free search list that lets customers request specific items, from tea carts to ’70s bathing suits. 1432 W Chicago Ave (312-526-3164).

This immaculate, uncluttered 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 items. Score everyday fashions such as white mid-’60s leather ankle boots ($70), a beige linen ’70s dress with leather belt ($45) and a belted, pink late-’70s puffy-sleeved top ($28). 1452 W Chicago Ave (312-243-3100).

If you don’t mind a little grime, Jan’s Antiques (225 N Racine Ave, 312-563-0275) could pay off amid the heaps of furniture, old radios, paintings and stained-glass windows. Vintage hounds can also hunt at nearby Chicago Antique Market, part of the monthly Randolph Street Market Festival (centered around the Plumber’s Hall building, 1340 W Randolph St). Aisle after aisle presents furniture from the 19th century to the 1980s, plus vintage clothing, decorative items and more.

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