I’ve Lived in Chicago for 15 Years—These Are My 15 Winter Must-Haves
Living in Chicago for the past 15 years has taught me a few crucial lessons about winter—like how to navigate icy sidewalks, appreciate a warm coffee shop, and most importantly, how to dress for survival without sacrificing style. When I first moved here, I naively thought that a puffer coat and a few sweaters would be enough. But after one especially brutal January where I found myself under-dressed in a snowstorm (rookie mistake!), I quickly realized that Chicago winters demand a different level of preparation. Over time, I’ve refined my winter wardrobe into a set of essentials that can handle anything from bone-chilling winds off Lake Michigan to the deceptively sunny-but-freezing days that always catch you off guard.
These essentials are more than just items in my closet—they’re the pieces that have become my cold-weather MVPs, making those endless gray days feel a little more bearable. From the perfect wool coat that I’ve been wearing on repeat for years to cozy cashmere sweaters that feel like a warm hug, each item is handpicked to keep me warm and stylish, no matter what Chicago throws my way. And let’s be real, in a city where winter often stretches well beyond its welcome, finding pieces that blend practicality with a touch of luxury is key. It’s taken a lot of trial and error (and more than a few frostbitten fingers), but I’ve finally cracked the code on what it takes to survive—and thrive—through a Midwest winter.
So, if you’re gearing up for another season of snow and sleet, or just looking for those winter wardrobe heroes that can stand the test of time, I’ve got you covered. Ahead, I’m sharing my 15 winter must-haves—the tried-and-true favorites that have kept me cozy, chic, and, most importantly, warm through 15 winters in the Windy City. Trust me, these are the pieces you’ll be reaching for on repeat from December through March (and sometimes April, because, well, Chicago).
A Classic Wool Coat
the constant™ coat
Double-breasted Italian melton wool coat
$398
There’s something about a classic wool coat that never goes out of style. It’s the piece that instantly pulls together any outfit, making you look put-together even when you’re shivering on the sidewalk. I’ve had my camel-colored coat for nearly a decade, and it’s still one of my most worn pieces during the winter months. The trick is to find one with a bit of extra length for that extra layer of warmth. It pairs just as well with a chunky sweater and blue jeans as it does over a sleek work dress. Trust me, this one’s worth the investment.
Down Puffer Jacket
Big Puff Coat
$124.00
I resisted puffers for years, thinking they were too bulky for my liking—until that first sub-zero day hit, and I quickly changed my tune. A down puffer jacket is absolutely essential for surviving Chicago’s coldest stretches. Look for one that’s lightweight but has plenty of insulation to keep out the chill. Bonus points if it’s water-resistant for those slushy days when the snow starts to melt. It’s my go-to for everything from errands to dog walks when staying warm is the priority.
Thermal Leggings
High-Waisted Fleece-Lined Leggings
$16.09
Layering is key to staying warm without looking like a marshmallow, and thermal leggings have become my secret weapon. I wear them under just about everything—jeans, trousers, even skirts—on cold days when I need that extra warmth. Plus, they’re perfect for adding some insulation without feeling too bulky. I always make sure to stock up at the beginning of the season because they tend to sell out quickly once the first snow hits. Trust me, once you try them, there’s no going back.
Cashmere Sweaters
JCrew
Brushed cashmere cropped V-neck sweater
$168.00
Nothing feels more luxurious on a cold winter morning than slipping into a cashmere sweater. It’s one of those winter wardrobe essentials that instantly elevates any outfit. I like to invest in neutral colors like cream, grey, and navy, which go with just about anything in my closet. Layer one under a leather jacket for a mix of cozy and cool, or wear it solo on milder days. They might come with a higher price tag, but they last forever if you take care of them—and they make those brutally cold mornings just a little bit cozier.
Knee-High Boots
Nine West Barile Boot
$189
There’s a reason knee-high boots are a winter staple year after year—they’re the perfect blend of style and functionality. They add a sleek touch to any outfit, whether you’re pairing them with midi skirts or tucking them into your skinny jeans. But they also do a great job of keeping your legs warm when you’re walking those windy streets. I look for styles that are made from genuine leather and have a bit of a heel for a more polished look. Trust me, these boots are worth the splurge if you want to stay stylish without freezing.
Insulated Winter Boots
Women's Everleigh Warm Lined Boot
$170
Forget everything you thought you knew about winter boots being bulky and unattractive. Today’s insulated winter boots come with sleek designs that don’t make you feel like you’re wearing snowshoes. My go-to pair has a rugged sole that grips icy sidewalks and keeps my feet warm even when the temperature dips into the negatives. Look for styles with waterproofing, because when Chicago’s snow turns into slush, there’s nothing worse than soggy feet.
Waterproof Chelsea Boots
These have been a game-changer for me. While I love a classic Chelsea boot for their sleek silhouette, I learned the hard way that leather alone doesn’t cut it in Chicago’s wet winter months. That’s why waterproof Chelsea boots are now a non-negotiable in my closet. They’re stylish enough to wear with my office outfits, but they also handle the unexpected slush puddles that appear around every corner. The best part? They pair just as well with skinny jeans as they do with midi skirts.
Stylish Knee-High Boots
Ninety Union Link Boot
$129
When I want to dress up a bit without sacrificing warmth, knee-high boots are my secret weapon. They add that extra layer of protection against the wind while giving my winter outfits a more polished look. I’ve found that a well-made pair can last for years, making them a worthy investment. Pair them with a sweater dress or slip them over faux leather pants for an easy, put-together look that’s ready for anything from dinner dates to weekend shopping.
Shearling-Lined Slippers
J Crew
Suede shearling lined slippers
$39.50
I know, slippers don’t exactly scream “outdoor chic,” but trust me—when you’re inside after a long, cold day, nothing beats slipping into a pair of shearling-lined slippers. They keep my feet toasty warm and are perfect for those lazy weekend mornings when I’m not quite ready to face the cold. I keep a pair by the door so I can swap out my boots as soon as I walk in. It’s a small luxury that makes a big difference during the coldest months.
Wool Socks
Target
Women's Midweight Snowfall Fair Isle 2pk Boot Socks - All In Motion
$12.00
This might seem obvious, but wool socks are the unsung heroes of winter dressing. I used to think any old socks would do, but after a few seasons of freezing feet, I finally upgraded to thick, cozy wool pairs—and I’ve never looked back. They’re the perfect match for my winter boots, adding an extra layer of insulation that’s essential when you’re braving the cold. Plus, they’re great for lounging around the house on those days when the weather outside is just too brutal.
Fleece-Lined Tights
Jcrew
Fleece tights
$12.00
These were a revelation for me. I used to think tights were only for fall, but fleece-lined tights changed the game. They’re perfect for adding an extra layer of warmth under midi skirts or even jeans during the coldest months. It’s amazing how such a simple piece can make a huge difference, especially when you want to keep wearing your favorite skirts and dresses well into the winter season. Plus, they don’t add bulk, so you still get that streamlined silhouette.
Lightweight Down Vest
Amazon
Button Down puff vest cotton padded jacket
$69.99
A lightweight down vest has become one of my layering MVPs. It’s that perfect middle layer that keeps my core warm without restricting movement or making me overheat. I love wearing one under my classic wool coat for extra insulation on those cold days. It’s also ideal for milder winter days when a full puffer is too much but you still need something more than a sweater. This piece is all about adding extra warmth where you need it most.
Merino Wool Base Layers
J.Crew
Machine-washable merino wool-blend turtleneck
$39.50
After one too many winters of piling on bulky sweaters, I discovered the magic of merino wool base layers. They’re lightweight, moisture-wicking, and so soft against the skin. The best part? They keep you warm without making you feel like you’re roasting the second you step indoors. I always keep a few long sleeves on rotation, perfect for layering under everything from sweater dresses to button-down shirts. Once you try them, you’ll wonder how you ever survived winter without them.
Thermal Tops
Old Navy
Plush-Knit Long-Sleeve T-Shirt
$19.99
It might sound basic, but a good thermal top is an essential part of my winter wardrobe. I look for ones that have a snug fit so they can layer easily under other pieces without adding bulk. They’re great for wearing under my chunky knit sweaters or even on their own on milder days. Whether I’m spending the day outside or working from home, these tops keep me warm and comfortable.
Cashmere Wrap
Uniqlo
Cashmere Scarf
$59.90
I never knew how much I needed a cashmere wrap until I had one. It’s like a blanket you can wear out in public—and honestly, who doesn’t want that when the windchill is below zero? I drape it over my shoulders on chilly mornings at home, then throw it over my coat when I head outside. It’s one of those versatile pieces that add a touch of luxury to your winter style while keeping you cozy. And it’s perfect for special occasions when you need something a little dressier than a bulky scarf.
