Everyday wearable underpinnings—that are still undeniably pretty—are consistently stocked at this Chicago institution.
Tucked away on a quiet stretch near DePaul University, Kaveri focuses on slightly adventurous cuts, like cropped Rag & Bone bombers and slouchy Demy Lee cashmere sweaters.
Styled like an '80s Afro-pop parlor, this newcomer specializes in wildly well-priced vintage pieces (it's hard to find anything that tops $40), including grandpa cardigans and Swatch watches.
The emphasis here is on costume jewelry—all arranged in the center of the store—but the bordering racks deserve a look, too, since they're lined with vintage party dresses, many from highly coveted names.
Truly old-world (it's been around since 1875), Merz stocks an intensive array of hard-to-find beauty labels, like 4711 (the world's first cologne) and Badger.
Occupying a garage-like, sun-drenched corner in the Meatpacking District, this looks like a gallery at first glance. Closer inspection reveals paper-thin, bright orange serving bowls and baskets from Mali.
This was one of our favorite boutiques in the country when Lucky launched more than a decade ago: It's still spot-on, offering labels like Winifred Grace, Lizzie Fortunato Jewels and 3.1 Phillip Lim.
Slightly retro, preppy standards by labels like A.P.C. set the tone here—while checkboard floors and midcentury-modern fixtures contribute to its schoolhouse vibe.
Hotel silver, historic Queen-emblazoned ashtrays from the U.K. and a smattering of ephemera add up to P.O.S.H.'s enduringly great Parisian-flea-market feel.
A pioneer in Chicago's quickly burgeoning West Town, Post 27—devoted to antiques and up-and-coming furniture and industrial designers—sits in a warehouse-size space but feels thoroughly intimate, thanks to expertly arranged mini areas.