Browsing through the piles of heavy costume jewels at this Wicker Park store feels a lot like rummaging through your grandma’s basement—that is, if your grandma also hoarded wares like 18th-century paintings (on sale for, uh, $85,000). The shop also stocks a handful of more budget-friendly home furnishings.
The main floor here houses a hipster-chic selection of menswear and womenswear (skinny jeans, jumpers and adorable jackets) with a vintage flair, but wind your way up the spiral staircase to the second floor to find the real-deal moth collectors.
Lenny & Me
Vintage and thrift attire (and occasional housewares) share the floor space in this rather sprawling resale store, where you can buy, sell or trade. Keep an eye out for steals like a gently worn Diane von Furstenberg wrap.
Owner Liz Meyer, a fashion stylist for Aerosmith, has compiled a beautiful collection of day wear and formal attire. Standouts include striped taffeta cocktail dresses from the 1950s, along with a heavy focus on Vivienne Westwood and an extensive selection of bridal gowns and veils from as far back as the Victorian era.
(1460 N Milwaukee Ave, 773-489-9428)
If you’re in the market for vintage (namely rust-colored) leather boots, start your search by perusing the dozens of kicks crowding this shop’s front window. Don’t mind the owner’s dog while you check out the dense selection of men's jackets of the leather, corduroy and wool variety.
(1472 N Milwaukee Ave, 773-772-4296)
Find everything from a two-piece ‘70s suit to a pillbox hat worthy of making a cameo at the Drake’s classy high tea. Chances are you’ll find a designer label or two tucked among the finely curated mix of mostly '40s to '80s attire and accessories.