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Vintage Underground

This subterranean space specializes primarily in vintage jewelry: The expansive selection is well sorted and well priced, which means you can snap up a great turquoise ring for $40.

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Stitch

There's an intensive array of Missoni home goods at this long-standing accessories emporium, but it finds fitting company with the equally luxe-feeling rainbow of Botkier bags and beachy, beaded Chan Luu bracelets.

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Sprout Home

At this store devoted to all things garden-related, you should definitely pay special attention to the wildly cool (and packable) terrariums, peopled with hilarious miniature figurines.

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Space 519

Sprawled out on the fifth floor of one 
of Michigan Avenue's main malls, this spot feels like a well-kept secret: Coffee-table books, rare European beauty products, cashmere sweaters and a smattering of cool antiques 
set the eclectic tone.

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Silver Moon

Antique 19th-century wedding dresses 
get top billing here, but the real pull is the racks up front, full of gorgeous, big-event gowns.

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R.S.V.P. Gallery

This below-ground spot is a street-inspired concept shop: Christopher Kane T-shirts, Thierry Lasry sunglasses and Hood by Air tanks abound.

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Robin Richman

When it comes to a subtly bohemian aesthetic—served up via Gary Graham's asymmetrical dresses and exotically tinged jewelry—Robin Richman always gets the city's top honors.

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Ravenswood Antique Mart

It may be a big antiques mart, but everything here feels special and handpicked: There's an entire case of owl medallions, plus design classics, like George Nelson clocks and Paul McCobb desks.

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P.O.S.H.

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.

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Penelope's

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.

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