What to Wear in Chicago, From 4 Stylish Locals

If you have a trip to Chicago on the horizon, you may be wondering what to pack and wear in the Windy City right about now. And if you don't, well, maybe you should, because apart from impressive architecture, mouthwatering food, and a serious sports scene, the city has shopping that shouldn't be missed.

According to a few of the boutique owners who cater to stylish locals, tastes tend to skew more casual than, say, New York—but especially with the often-chilly weather, beautiful, well-made sweaters, coats, and boots are essential, and accessories are best when they provide a pop of personality.

Below see how four of the city's coolest store owners characterize Chicago style (and no, not the Chicago Style you used to cite sources for college papers), plus shop the pieces that fashionable residents are scooping up this season.


There's plenty of personality packed into this East Village boutique run by husband-and-wife duo Joe Lauer and Jena Frey. Expect curated collections from cool indie designers in every section, plus an always-welcoming vibe.

How the owners describe Chicago style: "Clean, classic, relaxed, practical, and individual."

Penelope's, 1913 W. Division St.

"One style that we always try to stock for fall and does well for us is an overcoat, for those days when you want to look a little classier than your typical puffer or parka," says Frey. "We currently have a bunch from Sessun in a variety of materials, colors, and lengths"

"We are excited about lots of the amazing prints, patterns, and materials from some of our favorite American designers," says Frey, pointing to Ace & Jig, Samantha Pleet, and Dusen Dusen as standouts.

"Also, our French collections had a great season," she continues, citing A.P.C., Des Petits Hauts, Sessun, and Petit Bateau. "We currently have a lot of it hanging together at the front of the shop. There is a fun and cohesive color palette, compelling silhouettes, and classic French style."

Space 519

Chicago's most stylish denizens—plus reams of in-the-know visitors—flock to this arty concept store for curated pieces from around the world. Co-owners Lance Lawson and Jim Wetzel handpick everything from high-design home goods to clothing from labels like Protagonist and Tome, and in the spring, they're expanding to a 5000-square-foot flagship to stock even more of it.

How the owners describe Chicago style: "NYC sophistication meets L.A. ease," says Lance. "Ladies in Chicago want what is cool and new, but they want it to work into their everyday lifestyle," says Jim.

Space 519, 900 N. Michigan Avenue, level five in the 900 Shops (200 E. Chestnut St. as of March 2018)

This is "the perfect-fitting high-waisted jean in a vintage wash," say the owners.

"'80s-inspired statement earrings" are on track to be big news this season.

These sell year-round "since Chicago can be a sweater city 10 months out of the year."


Hit this Wicker Park shop, and you're sure to discover a new favorite under-the-radar brand. Owner Tricia Tunstall makes it easy with an edited mix of wearable basics, eye-catching accessories, and fashion-forward statement pieces.

How the owner describes Chicago style: "Individualistic, fashion-forward, practical, and confident."

p.45, 1643 North Damen Avenue

Tunstall says a "utilitarian boot with an edge" always sells well with Chicagoans.

The "juxtaposition of sparkle and glitz with classic fabrics" is a must-try for fall.

Rep the city in style with this coat from French designer Floriane Fosso.

Up next: The best flats to wear to the airport, according to Blake Lively.