Must-Shop Boutiques in Downtown Chicago

Courtesy of Alice & Olivia

By Kristin Lee Jensen

Every city puts its own spin on the latest trends in fashion. Come fall, Chicagoans have a way of embracing every new style for as long as the weather holds out. The best-dressed ladies will gladly keep their black North Face down jackets stowed away and flaunt chic black boots, patterned tights and skinny scarves.

This season, take your fashion cues from locals and visit downtown-area boutiques that pair comfort and function with bold, conceptual designs. Alice & Olivia, for instance, offers high-waisted bell pants and oversized ponchos, while Tory Burch splashes tapestry patterns across long-sleeved dresses and billowy tops. “Other places are Zara and Topshop,” explains Bobby Gonzalez, concierge at Hotel Palomar Chicago.

With more than 450 shops on the Magnificent Mile, sartorial travelers need not go far to find definitive styles. At the northern boundary by Oak Street, luxury brands anchor the famed avenue, while Chicago classics and chic designers abound further south on the 13-block stretch.

Regardless of personal style, shoppers will find fashionable additions to their fall outfits hanging in a nearby boutique downtown. Stay in vogue regardless of the seasonal chill that settles over the Windy City—there’s sure to be a cropped coat or belted trench on the racks to keep you warm while you strut your stuff down the streets.


Near North Side

Fashionistas can update their fall wardrobes in the upscale boutiques nestled at the north end of the Magnificent Mile by Oak Street.

Courtesy of Alice & Olivia
Courtesy of Alice & Olivia

1. “All the luxury brands are concentrated north of the Water Tower near Oak Street. ST. JOHN is there. It is for discerning women looking for a specific item. It’s still a beautiful store with beautiful clothing that everyone should check out.” Multiknit jackets, floral fil coupe coats and Jacquard dresses abound at this classic boutique. (919 N. Michigan Ave.; 312-943-1941; —Alex Abello, concierge at Fairmont Chicago, Millennium Park

2. “There’s TORY BURCH on Oak Street—that’s where the trendy, upscale women’s boutiques are. The boutique is not in [a] shopping center; it stands by itself on Oak Street.” Inside, shoppers can peruse a trove of definitive clothing, as well as leather and chic accessories. (45 E. Oak St.; 312-280-0010; —Kathy McClanathan, chef concierge at InterContinental Chicago

3. “I like ALICE & OLIVIA because it’s classic with a spunky, fun kind of twist, and the girls that work there are very helpful and great with putting outfits together that I wouldn’t have thought of otherwise.” Helmed by designer Stacey Bendet, the brand has been worn by modern-day fashion icons, including celebrities Gwyneth Paltrow, Beyoncé, Sarah Jessica Parker and first lady Michelle Obama. (919 N. Michigan Ave.; 312-273-1254; —Front desk staff at Hotel Allegro Chicago


Surrounding River North

Move south along the Magnificent Mile to update your outfit with styles from the city’s top brands.


1. “There’s a series of shops in Chicago called AKIRA. There are a number of locations in and around the city. It’s always on the cutting-edge of trendy fashion. Akira has clothing and footwear, and it’s always the latest styles. It has a reasonable price point, but it’s still upscale.” Though the first boutique launched in the Wicker Park/Bucktown area, it’s since opened a shop inside Water Tower Place. (835 N. Michigan Ave.; 312-951-5508; —Kristen Klus, chef concierge at Four Seasons Hotel Chicago

2. “There’s a really cool shop off the Magnificent Mile called MARLOWE. It’s a clothing store, and it’s very high-end, very prestigious.” With a heightened focus on clean lines, this brand marries high-quality cashmere knitwear with bespoke, finely tailored sportswear for the elegant woman. (800 N. Michigan Ave.; 312-988-9398; —Alex Abello, concierge at Fairmont Chicago, Millennium Park

3. “IKRAM is a Chicago classic. It’s not just for shopping; it’s really a total experience. It’s very fashion-forward with very interesting pieces that are almost like art. They also have a great cafe there. If someone is looking for a shopping destination in Chicago, that would be where I send them for something totally unique.” The high-end boutique also features an expansive shoe selection with styles by designers including Jimmy Choo, Manolo Blahnik and Robert Clergerie, among others. (15 E. Huron St.; 312-587-1000; —Gianna Bamonti, assistant chef concierge at The Peninsula Chicago