One of the greatest aspects of Chicago is that it’s an incubator for creative types. From award-winning culinary notables to tech stars, the Windy City’s scene is constantly pulsing with energy.
That’s especially true when it comes to personal style, which makes people-watching in the Chi extra chic. Whether you’re roaming the streets of the uber-touristy Magnificent Mile or hipster Wicker Park, do you ever wonder where to get all those great looks?
Here are some of the best shopping destinations around Chicago.
Go Vintage
10 minutes from downtown, Wicker Park and Bucktown continually lay claim to some of the best shopping in the city, but with the likes of chains like American Apparel, BCBG and Marc Jacobs infiltrating— many of the locally owned, more edgy boutiques have been forced to shutter. Thankfully, quite a few have gained the support of the community and have become citywide institutions. Head to six corners (the intersection of Milwaukee, Damen and North Ave.) for a mix of thrift shops and trendier staples like Urban Outfitters.
The area’s frugal fashionistas will appreciate Angelique’s (1330 N. Milwaukee Ave.), a flirty find showcasing colorful dresses, tops and accessories. Expect to spend more at the luxurious Robin Richman (2108 N. Damen Ave.), a gallery-like boutique dominated by unique dresses, handbags, shoes and jewelry that you won’t find back home. Sharp-dressed Chicago men head to Apartment 9 (1804 N. Damen Ave.) for micro-tweed sweaters, double-striped polos and Indigo wash denim. Shop the sassy dress selection at Kiz (2035 W Division St.) then hit nearby Fluevog (1539 N Milwaukee Ave.) for some truly unique kicks.
See and be Scene
Over in the Gold Coast/River North neighborhoods, the style is best characterized as high-end. There’s the Burberry flagship store (633 N. Michigan Ave.); Jimmy Choo (63 E. Oak St.) on Oak Street; plus the iconic malls of the 900 North Michigan Shops (900 N. Michigan Ave.), The Shops of North Bridge (520 N. Michigan Ave.) and Water Tower Place (835 N. Michigan Ave.), that make up the 13-block stretch of Michigan Avenue. With more than 460 stores, 275 restaurants, 60 hotels, and unique attractions in the area, it pretty much defines downtown Chicago and is a destination for all things designer.
Browse the Boutiques
While independently owned boutiques are scarce in the Gold Coast/River North area, the ones that are there have thrived. Great for seeking out one-of-a-kind pieces from lesser-known designers, these establishments are no less luxury. Haberdash (611 N. State St.) showcases a nice mix of local and international fashion up-and-comers, while Perchance (11 E. Walton St.), adjacent to the Waldorf Astoria, caters to its clientele with everything from sequined cocktail dresses to tie-dye tunics. Sofia (100 E. Walton St.) specializes in beautiful baubles that pair well with party dresses and standout evening gowns.
Another place to pull together a great look without trying too hard is Ad Hoc (1948 W. Chicago Ave.), a groovy little space in West Town, featuring fashion, artwork, jewelry and more. Sure, they sell skinny jeans and graphic tees, but they come with a trendsetter attitude that’s easy to adopt.
Local Labels
Akira is a local gem with outposts throughout the city. Besides offering a collection of over 200 brands like Jeffrey Campbell shoes, For Love and Lemons, Mink Pink, Senso shoes, OCC Lip Tar, One Teaspoon, Jessica Simpson shoes, Melissa footwear, and BCBG, they also have their own in-house label that’s an affordable, fashion-forward “adult” version of Forever 21.