Oak Street

Called the Rodeo Drive of Chicago, Oak Street houses some of the city’s most prominent high-end retailers. Located in the historic Gold Coast neighborhood, the area is one of the most affluent enclaves in the city. For that reason, visitors and locals alike can shop the tree-lined street for such designers as Hermes, Prada, Chanel, and Dolce & Gabbana.

The Oak Street Neighborhood

Oak Street is adjacent to Michigan Avenue, north of the Magnificent Mile shopping area. Oak Street, including the surrounding Rush and Walton Streets, is its own upscale retail district. Oak Street has more high-end shopping than Magnificent Mile, housing luxury brands, international fashion brands, and designer boutiques.

This gem is also more intimate than the staggering Magnificent Mile, with narrower tree-lined streets that see less foot traffic. It features many of the historic stone mansions built by Chicago’s wealthiest residents in the late 1800s. Along with the prestigious shopping, some of the city’s best-known restaurants are here as well, including Lou Malnati’s Pizzeria, the Pump Room, and the original Morton’s.

Of course, those who stay here receive the royal treatment as well. The Drake, the Knickerbocker Hotel, Viceroy and the Waldorf Astoria, are several of the high-end accommodations located in the Gold Coast neighborhood, near Oak Street.

Nearby, you’ll also find sites worthy of the Gilded Age including the Driehaus Museum, Museum of Contemporary Art, and Newberry Library. 

The Oak Street Shops

To enjoy an afternoon shopping the designer offerings on Oak Street, start on the west end at North Rush and Oak Street. There, you’ll find Hermés, the French luxury designer best known for exquisite silk scarves. You’ll also find an array of apparel, leather goods, and handbags at the iconic atelier.

Next door is the Italian luxury counterpart to the French Hermés, Georgio Armani Chicago. The fashion retailer sells high-end apparel and accessories from the namesake designer, with European sensibility. Or, stock up on luxe down jackets and sportswear from the French-Italian Moncler.

The Italian flair continues at Loro Piana, with its high-end luxury wool and cashmere. Across the way, contemporary style rules the look at COS, stocked with reinvented classics and wardrobe essentials inspired by art and design. Representing American designers on the strip is Tory Burch, stocked with the designer’s chic women’s clothing, shoes, and accessories.

For minimalist style, shop VMR for contemporary luxury fashion designers stocked from around the globe. More European sensibility enters at Escada, the luxury women’s designer clothing company hailing from Munich, Germany.

Next door, find Milan-based jewelry house Buccellati, where shoppers can buy luxury watches, bridal, engagement rings, and even silverware. Then, Tom Ford brings cutting-edge apparel, accessories and cosmetics for men and women to the shopping scene.

Of course, children need to be well outfitted as well. Milani Boutique features designer clothing, shoes, and gifts for children and infants. Across the way, Maje sells ready-to-wear for women, positioned next to trendy American designer Rebecca Minkoff. Vince is also in this plaza, selling timeless, chic clothing for men, women, and children.

Across the way, gents can shop posh menswear at the luxe haberdashery, Paul Stuart. It is positioned next to casual, on-trend sporting shop, Athleta. Toward the east end of the luxe street, you’ll find Tod’s luxury Italian shoes and accessories as well as St. John Boutique, stocked with sumptuous knitwear.

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