Chicago Shopping Guide

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On the shores of Lake Michigan is this leafy, upscale North Shore community, known for its outstanding shops dedicated to rising designers.


This younger cousin of old-guard Winnetka boutique Frances Heffernan stocks pieces that have a sense of quiet luxury: soft leather Henry Beguelin totes, Alexander Wang cocktail dresses, and Temple St. Clair gold amulet necklaces. The decorative elements of the space—simple aluminum fixtures, a wall-size chalkboard regularly updated with news of the store's latest arrivals—contribute to Frannie's overall relaxed, welcoming feel. One perk of shopping here is the in-house alteration department: A fleet of eight respected seamstresses are at the ready (and can turn around garments in record time).
808 Elm St., 847-446-5508

Products: Women's Clothing, Bags, Jewelry
Type of Store: Boutique


It's not often that a boutique expands from the suburbs into the city, but that's exactly what happened with Winnetka-based Gray, which unveiled its second location in Chicago's Old Town early last year. As winning as that outpost is, we have a soft spot for the original. Catherine Malandrino, Milly, Tracy Reese, Nanette Lepore, and Harkham are just a sampling of the feminine lines on offer. Regardless of season, Gray always carries a staggering number of dresses, followed closely by pretty tops. There's no shortage of premium denim, either: Currently, a full range of styles is available, from dark-wash drainpipes to trouser-cut wide-legs.
821 Chestnut Ct., 847-446-5650

Products: Women's Clothing, Denim, Bags
Type of Store: Boutique


New to the village is the latest branch of this wildly popular Chicago minichain. And as with the other Jake locations, it has a modern Hollywood Regency look—red lacquer cabinets, ornate oversize mirrors, chrome starburst chandeliers—and crisply minimal clothing hanging from brushed-metal racks. This season, Thread Social, Mayle, and Lutz & Patmos have designed garments exclusively for the store, and they perfectly complement the selection of citified pieces by Doo Ri, Bruce, and Nili Lotan (also be sure to check out Barbara Bui bags and Bing Bang jewelry). Out-of-towners can be part of the action, too: Jake has an outstanding companion website (see address below).
565 Lincoln Ave., 847-501-5253,

Products: Women's Clothing, Bags, Jewelry, Shoes
Type of Store: Boutique


With a salon full of designer shoes visible through its giant plate-glass windows, it's difficult not to be drawn in by this upscale standard. But the patent Lanvin ballet flats and buckled Chloé pumps are just the beginning: Within Neapolitan's roomy, warmly minimal space are a wall of luxe bags (Bottega Veneta woven-leather hobos, Alexander McQueen "Novak" clutches) and a well-edited selection of garments from Derek Lam, Brian Reyes, Zac Posen, and Nina Ricci.
715 Elm St., 847-441-7784,

Products: Women's Clothing, Bags, Shoes
Type of Store: Boutique