Chicago has long been touted for its progressive theater and food scene, but the young fashion landscape is equally vibrant. What used to be a sea of Midwestern twin sets has morphed into a supremely chic retail environment that is arguably as au courant as Los Angeles or New York. From indie boutiques in up and coming neighborhoods to the top tier designer flagships that populating the Magnificent Mile, fashion in Chicago will not disappoint. The best retail areas stretch from the southern tip of the Chicago River and extend down Michigan Avenue, before branching out through the Gold Coast. Here you will find Saks, Barneys, Neiman Marcus, Nordstrom, Top Shop, and high wattage local fashion purveyors like Blake and Ikram. Oak Street is Chicago’s Rodeo Drive chockoblock with A-List destinations includng Hermes, Jimmy Choo, and Dolce & Gabbana. Check out the heavily foot trafficked Rush Street for smaller shops like Scoop and Intermix.
Visit T+L’s Guide to Shopping in Chicago for more inspiration.
George Greene is the Savile Row meets Fred Segal of Chicago. Discerning clientele flock to this menswear mecca for custom-Kiton suiting, Luciano Barbera, Belstaff, Yohji, Thom Brown, and contemporary pieces like Chrome Hearts. Killer merchandise combined with incomparable service and a charming ambiance (potted palms, ancient leather club chairs, and hardwood floors) are the mark of true haberdashery.
Ikram Goldman, Michelle Obama’s former stylist and major duomo of the enormous, red lacquer sartorial sanctuary bearing her name, can only be described as legendary. Top-tier fashion mavens snap up pieces from iconic designers (she has exclusives with many) and need-to-know artisans like Creatures of the Wind, Rodarte Rogue Bespoke, Sacai, Rick Owens, Loree Rodkin, and Zero Maria Cornejo.
For over thirty years, Dominic Marcheschi and Marilyn Blaszka have been fashion pioneers. Together, they’re bringing the crème of the runway crop to Chicago. Beloved for their edgy and eclectic taste, this River North boutique (a renovated post office) is filled with a thoughtful curation of Balenciaga, Marni, Dries, Veronique Margiela, and lesser-known European talent.
Luxury Garage Sale
There is an incomparable thrill divined from scoring designer duds at a fraction of their retail cost—especially without a lingering scent of camphor. Luxury Garage Sale is a glam, upscale consignment shop selling contemporary (Missoni, Tory Burch, Diane Von Furstenberg) and vintage (Yves Saint Laurent, Chanel, Hermes) clothing and accessories in pristine condition.
Like its NYC cousin, Barney’s Chicago is a bright, airy, and whimsical shopper’s paradise committed to showcasing all that is trending from the Americas and abroad. Five floors are flawlessly curated, and feature the most recognized designers, contemporary sportswear, and high-end beauty brands. The shoe department is one of the best in the city.