Edgewater Antique Mall
A recent trip to this expansive antiques mall turned up both a Coogi sweater from the '80s and a rainbow's worth of Bakelite bracelets.
6314 N. Broadway St., 773-262-2525, edgewaterantiquemall.com
6314 N. Broadway St., 773-262-2525, edgewaterantiquemall.com
Eskell
It's one of Chicago's big success stories (the label is sold at some of the best boutiques in the States), so it's no surprise that the Eskell flagship is equally cool: Beyond the beautifully patterned in-house line, there's a great array of nicely priced labels like Minkpink.
1509 N. Milwaukee Ave., 773-486-0830, eskell.com
1509 N. Milwaukee Ave., 773-486-0830, eskell.com
Greer
A giant oak library counter and antique card catalogs make it feel like a study, appropriate since Greer is exclusively devoted to exquisite stationery, journals and pens.
1657 N. Wells St., 312-337-8000, greerchicago.com
1657 N. Wells St., 312-337-8000, greerchicago.com
Helen Yi
Helen Yi has been one of Chicago's fashion pacesetters for nearly a decade, and somehow it's lost none of its edge: Gorgeously tailored Derek Lam blazers mingle with feminine blouses by Barbara Bui.
1645 N. Damen Ave., 773-252-3838, helenyi.com
1645 N. Damen Ave., 773-252-3838, helenyi.com
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.
1834 W. North Ave., 773-252-4559, chicagovintageunderground.com
1834 W. North Ave., 773-252-4559, chicagovintageunderground.com
Asrai Garden
Moodily lit and decked out in foliage, this flower shop/gift store feels extravagantly lush, just like its handmade, embroidered necklaces and artisanal candles.
1935 W. North Ave., 773-782-0680
1935 W. North Ave., 773-782-0680
Blake
This is the best spot in town for avant-garde labels—Dries Van Noten, Marni—and equally forward finds, like Nicholas Kirkwood heels.
212 W. Chicago Ave., 312-202-0047
212 W. Chicago Ave., 312-202-0047
Brimfield
This newish home goods spot looks like an English countryside antiques shop that's had a run-in with a Native American trading post. Highlights include footstools upholstered in iconic Hudson Bay prints.
5219 N. Clark St., 773-271-3501
5219 N. Clark St., 773-271-3501
Broadway Antique Market
A maze-like array of cases, packed with blown-glass vases, enamel Chicago charms and prints from the '60s, makes it easy to spend a whole afternoon here.
6130 N. Broadway St., 773-743-5444, bamchicago.com
6130 N. Broadway St., 773-743-5444, bamchicago.com
Chalk Boutique
Though it's officially situated in the burbs, Chalk has a citified feel. Patchwork Chris Benz skirts hang next to slick black pants (artfully turned out by Olivier Theyskens for Theory).
2611 Prairie Ave., Evanston, 847-424-0011, chalkofevanston.com
2611 Prairie Ave., Evanston, 847-424-0011, chalkofevanston.com

