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what to wear in chicago
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What to Wear in Chicago

Chicago’s fluctuating weather—sometimes amounting to dramatic temperature drops in a single day—is legendary. That’s why Chicagoans often say if you wait five minutes the weather will change. For visitors wondering what to wear in Chicago, there’s a one-word answer, no matter the time of year: layers.

What to Wear in Chicago

Chicagoans regard their seasonal weather patterns as endless fashion opportunities. Below are the wardrobe staples most well-dressed locals own.



The versatile White Sierra Women’s 4 in 1 Jacket is as changeable as Chicago’s weather. The waterproof, hip-length nylon jacket offers several outerwear options in one. You can remove or reverse the quilted liner, which doubles as a stand-alone coat. The hood is detachable, and deep pockets easily store not only a phone, but also gloves and a hat. There’s a men’s version, too.


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A Chicago clothing essential, denim pants, skirts, and jackets of any style and color are en vogue year-round. Fashion-conscious Chicagoans like skinny jeans and stretchy jeggings worn with kicky ankle or knee-high boots. (Or straight-leg jeans and chukka boots for men.)

Capri Pants


A three-season pant, capris transition Chicago locals and visitors through spring, summer, and fall. Options include cargo-style for men and classic lightweight women’s styles.

Walking Shoes


Comfortable footwear is what to wear in Chicago for hours of exploring. Good foot support doesn’t mean sacrificing style when wearing Naturalizer footwear for all seasons.

Large Scarf


Hometown poet Carl Sandburg called Chicago the City of Big Shoulders, and while you’re here you’ll want a stylish wrap to cover your own shoulders, whether in winter cold or the chill of summer air conditioning. A light wool or pashmina scarf draped around the neck adds warmth and a touch of texture and color for both men and women.

Zip Pants/Shorts


Zip from warm-weather casual to cool night out in convertible pants from Columbia, available in multiple colors for men, women, and kids. A concealed zipper at the knee detaches at the pant’s calf, turning the wrinkle-resistant slacks into knock-around shorts.



(Photo: Amazon)

For fall and winter, a pair of stylish, practical boots is what to wear in Chicago. Try Sorel men’s and women’s boots for sensible Windy City style.



Flattering and comfortable, this mid-length skirt with shorts consists of shorts covered by a skirt made of no-wrinkle, quick-drying material. Deep side pockets fit a larger phone, cash, and keys. Thread an earbuds cord through the concealed opening in the waistband.



Any warm hat that covers your ears is what to wear in Chicago when temps dip. But a slouchy beanie is much more fun. The unisex cotton beanies are lightweight but warm, and come in both understated and vibrant colors.

Sports Team Apparel


Living in a city with several championship sports teams, Chicagoans appreciate fan fashion. Visitors are welcome to wear their favorite team’s logo, but Chicago sports apparel is a souvenir that never goes out of style.

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—Original reporting by Kit Bernardi

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