What to Wear in Chicago, From 4 Stylish Locals

Hilary George-Parkin

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.

Explore: Chicago, Shopping

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