Housed in a former post office, this expansive boutique 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
Bringing an urban edge to Chicago's north shore, Chalk carries beautifully made apparel and accessories by such established designers as Nina Ricci, The Row and Chloé. For the fashion enthusiast, Chalk also showcases edgier collections like Isabel Marant and Rosie Assoulin.
2611 Prairie Ave., Evanston, 847-424-0011, chalkofevanston.com
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
Originally a small gift shop, this long-standing neighborhood favorite occupies two enormous attached storefronts, and each has a distinct identity. The original space sells prettily packaged candles along with nicely priced tops and dresses; the lofty second chamber adopts a modern exoticism as its theme, with Turkish glass lanterns and color-splashed garments.
1706 N. Wells St., 312-751-2929, handlewithcarechicago.com
On Chicago's Gold Coast, Ikram Goldman's laquer red boutique is a beacon for the city's intelligentsia. Past the porthole-like entrance, we delved into lush Lanvin ruffles, sleek Céline frocks, and Marni belts studded with lozenge-like stones. It's no wonder a certain First Lady is a fan.
Krista Kaur Meyers' light-flooded corner store—a onetime insurance office—has an easy-flow split-level layout: The upper half showcases the latest from labels like Elizabeth and James and Helmut Lang (plus a small selection of footwear and accessories); the wares downstairs fall into the more casual, jeans-and-tees camp.
3458 N. Southport Ave., 773-248-1967, kristak.com
This mom-and-pop store closes for two months at the start of every year while the owners take a buying trip to a far-flung locale. They come back with amazing jewelry and accessories, most under $40.
801 Dempster St., Evanston, IL, 847-475-8665
Done up with chiffon pink shag carpets, milk-glass lamps, and a circular faux-ostrich couch, this boudoir-influenced spot presents clothing as unabashedly feminine as the decor. Missouri native Samantha Mittelman has long been a fan of traditional glamour and has put a modern-day stamp on the aesthetic through her classically flattering picks.
64 E. Walton St., 866-951-5383, samanthachicago.com