Exploring Oak Street: The Luxury Shopping Mecca in Chicago

Known as Chicago’s equivalent of Rodeo Drive, Oak Street serves as a hub for some of the city’s most distinguished luxury retailers. Situated in the historic Gold Coast district, this location stands as one of the most prosperous urban sectors within the city. As such, both tourists and residents have the opportunity to experience premium shopping on the picturesque tree-canopied street, housing fashion powerhouses such as Hermes, Prada, Chanel, and Dolce & Gabbana.

The Oak Street Vicinity

Positioned adjacent to Michigan Avenue and located to the north of the bustling Magnificent Mile shopping district, Oak Street, together with its neighboring Rush and Walton Streets, forms a unique high-end retail sector. In fact, Oak Street boasts a greater concentration of luxury shopping options than the Magnificent Mile, hosting a myriad of luxury brands, global fashion labels, and designer boutiques.

This jewel of Chicago offers a more personal experience than the sprawling Magnificent Mile, featuring narrower tree-shaded avenues with a lower volume of pedestrian traffic. It proudly showcases several historic stone mansions constructed by the city’s affluent citizens in the late 19th century. In addition to its superior shopping experience, the area also boasts some of the city’s top-rated eateries, such as Lou Malnati’s Pizzeria, the Pump Room, and the original Morton’s.

Naturally, those residing here are also treated to a luxurious stay. A number of high-class lodgings, including The Drake, the Knickerbocker Hotel, Viceroy, and the Waldorf Astoria, can be found within the Gold Coast district, in close proximity to Oak Street.

In the vicinity, you can also discover landmarks reminiscent of the opulent Gilded Age, including the esteemed Driehaus Museum, Museum of Contemporary Art, and the Newberry Library.

The Boutique District of Oak Street

Immerse yourself in an afternoon dedicated to shopping through designer merchandise on Oak Street, commencing from the western edge at North Rush and Oak Street. Here, you’ll discover Hermés, the distinguished French luxury brand famed for their stunning silk scarves. This renowned fashion house also provides an assortment of clothing, leather products, and designer handbags from their legendary workshop.

Adjacent to Hermés is the Giorgio Armani Chicago, Italy’s equivalent in luxury to the French Hermés. This premier retailer offers upmarket apparel and accessories from the eponymous designer, all radiating a European elegance. Alternatively, you can acquire luxury down jackets and sportswear from the French-Italian label, Moncler.


The Italian touch persists at Loro Piana, celebrated for its ultra-luxury wool and cashmere. On the opposite side, COS rules the scene with its modern style, offering a collection of revamped classics and wardrobe must-haves that draw inspiration from art and design. Representing American design on the strip is Tory Burch, fully stocked with the designer’s trendy women’s attire, shoes, and accessories.

VMR caters to lovers of minimalist style, offering contemporary high-end fashion pieces from designers across the globe. Adding another dose of European sophistication is Escada, the luxury women’s designer wear brand originating from Munich, Germany.

Next to it, you’ll find the Milan-based jeweler Buccellati, where you can purchase high-end watches, bridal and engagement rings, and even silverware. Meanwhile, Tom Ford contributes to the shopping extravaganza with its innovative clothing, accessories, and cosmetics for both genders.

Children’s fashion is not forgotten. Milani Boutique presents designer clothing, footwear, and gifts for children and infants. Across the way, Maje offers chic ready-to-wear for women, located alongside trendy American designer Rebecca Minkoff. Vince is also part of this shopping enclave, offering timeless, stylish clothing for men, women, and children.

Men can indulge in upscale shopping at the elegant Paul Stuart haberdashery, conveniently located next to the casual and current sporting shop, Athleta. Moving toward the eastern end of this high-end street, you’ll encounter Tod’s, offering luxury Italian shoes and accessories, and St. John Boutique, renowned for their lavish knitwear.

Oak Street

  • Address: E Oak St. and N Michigan Ave.
    Chicago, IL 60611

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