5 Layering Pieces I Swear By to Survive Chicago Winters in Style
Let’s face it: Chicago winters are basically a personality test. If you can survive the icy winds whipping down Michigan Avenue without crying, you’ve passed. But staying warm here isn’t just about survival—it’s an art form.
Over the years, I’ve learned that dressing for winter in Chicago is all about strategy. Pile on too many layers, and you look like a marshmallow. Too few, and you’ll regret every life choice by the time you reach the corner. The good news? I’ve cracked the code for staying cozy and stylish, even when it’s so cold your eyelashes freeze.
Here are five layering essentials that have saved me from countless frigid mornings—and no, they won’t make you look like the Michelin Man.
Thermal Base Layers That Actually Work
A good base layer is like an invisible superhero. You don’t see it, but you feel its power. I swear by merino wool and fleece-lined tops and leggings—they keep you warm without turning your outfit into a sauna. Slip them on under your clothes, and suddenly that walk to the train isn’t so miserable.
Banana Republic
Italian Blend Cropped Sweater
$200
Old Navy
Polo Sweater
$44.99
A Lightweight Down Vest for Extra Warmth
Think of a down vest as the MVP of winter layering. It keeps your core toasty without adding bulk to your arms (because who wants to feel like they’re in a snowman costume?). Plus, it works with everything—throw it under your puffer coat for extra warmth or over a sweater on a slightly less arctic day.
Tuckernuck
Black Jackson Quilted Vest
$138
Tuckernuck
Tan Sherpa Wilson Vest
$248
A Wool Coat That’s Warm and Chic
Finding a warm coat that doesn’t scream “ski trip” is no small feat, but a belted wool coat does the job beautifully. It’s like the little black dress of winter outerwear—timeless, versatile, and always appropriate. Bonus points if it’s long enough to cover your legs on those wind-tunnel streets.
Polo Ralph Lauren
New Heather Grey Wool Cashmere Blend Insulated Coat
$698
Tuckernuck
Camel Wool Cassidy Jacket
$248
Oversized Scarves That Double as Blankets
An oversized scarf is my winter survival kit. It’s a scarf! It’s a shawl! It’s a blanket when you’re stuck waiting for the bus! I wrap mine around my neck about three times and pretend I’m in a cozy cocoon instead of braving subzero temps. Pro tip: go for something soft enough that you won’t mind it brushing against your face all day.
Tuckernuck
Hot Pink Cashmere Blanket Scarf
$198
David and Young
Exclusive Blackwatch Tartan Ruana Poncho
$68
Fleece-Lined Leggings You’ll Want to Live In
Let’s be honest—jeans don’t always cut it when it’s negative a million degrees outside. Fleece-lined leggings, however, are the real MVPs. Wear them under skirts, dresses, or even jeans for an extra layer of warmth, or rock them solo with boots and an oversized sweater. Bonus: they feel like pajamas but look way more put-together.
Perfect Moment
Black Aurora Skinny Stirrup Race Pant
$490
