How to Dress for Winter and Still Look Cute

BY: Anam Ather |Jan 11, 2017

Dark-skinned woman wearing stylish winter clothes and knee-high boots

I’m a California girl through and through. Growing up on the West Coast, I never really had to think about how to dress for winter. “Winter” is a largely abstract concept in California where you can still take in sunsets from the beach, wander among palm trees, and do everything you do in summer. You just do it in a lightweight trench and scarf—and if I’m being totally honest, the scarf was purely for aesthetics.

And then I moved to Chicago.

Chicago, home to blizzards so bad they’re given charming pet names like “snowmageddon” and “snowpocalypse.” My first winter here was a crash course in learning how to dress warmly and withstand sub-zero temperatures. But I soon learned that just because the weather was blah didn’t mean my outfit had to be. I’ve developed some strategies for rocking a killer look without sacrificing precious body heat.

Shop Coats and Outerwear at Groupon

Here’s what my Chicago winters have taught me: the easiest way to stay warm while looking cool is to think of the season as three temperature categories. If you know which one you’re in for, your next step is to find a functional coat that matches your personal style. With the right coat, reverse-engineering your outfit is easy.

Mild Winter (40º–60º F)

Trench Coat | Faux-Fur Vest | Leather Jacket | Cotton Parka | Anorak

mild winter women's outfit leather jacket faux-fur vest distressed jeans booties choker

A leather jacket and faux-fur vest combo layers you for changing temperatures
and creates an edgy vibe with distressed denim jeans, khaki booties, and choker

Much like dressing for the crisp, cool days of fall, the key here is to layer your outfit. Dress so you can easily subtract or add pieces, as the temperature is likely to vary throughout the day. Pairing lightweight layers under versatile pieces such as a leather jacket or a classic trench coat are a great way to rock trendy looks that never go out of style. To up the ante, try layering a faux-fur vest (or military-inspired vest) over a leather jacket and an all-black ensemble for a chic, straight-out-of Paris vibe.

Moderate Winter (10º–40º F)

Pea Coat | Down Coat | Puffer Jacket | Double-Breasted Coat

moderate winter women's outfit pea coat cable-knit sweater blanket scarf over-the-knee boots fedora

With a pea coat providing the warmth, accent a cable-knit sweater
with blanket scarf, over-the-knee boots, and fedora

‘Tis the season to bundle up! When the dropping temperatures make you feel like you’re trapped inside a snow globe, it can easily start to feel like you’re getting lost underneath multiple layers of clothing. The trick here is to focus on the things that make you look and feel good. Quality materials such as leather, tweed, or velvet are ideal for keeping you warm and often come in flattering and tailored silhouettes that will also score you major style points.

Extreme Cold (Below 10º F)

Sherpa-Lined Parka | Quilted Coat | Wool Jacket

extreme cold weather women's outfit puffer jacket turtleneck dress fleece leggings pompom beanie hat snow boots

For maximum warmth (and minimum bulk), keep it sleek under a puffer jacket
with turtleneck midi dress and fleece-lined leggings—but accessorize for the weather

There’s cold, and then there’s feel-it-in-your-bones cold. When temperatures start dropping into single (or even negative) digits, it’s hard to want to do anything other than snuggle up next to the fireplace. Thankfully, you have your pick of durable functional outerwear that’s designed to help you withstand the harshest mercury plunges. Only downside? Parkas, down jackets, and similar coats naturally have a bulkier silhouette. To avoid a frumpy appearance, start with your choice of coat and—instead of donning thick layers—try wearing multiple light, form-fitting layers which help retain heat a lot better. A turtleneck midi dress and fleece-lined leggings are an excellent go-to outfit, since they conceal any additional base layers you might need.



Women's hats accessories earmuffs fleece headband knit headband knit beanie

Ear-puffs | knit headbands | fleece headbands | chunky beanies

The idea that you lose most of your body heat through your head might be an old wives’ tale, but just in case—load up on accessories to keep your head (and the rest of your body) warm. For the hair-conscious, options such as an embellished knit headband or a fleece ear-warmer do a great job of protecting your forehead and ears without ruining hairstyles. And for those trying to conceal a bad hair day, chunky beanies offer double-duty functionality while also giving you a casual-cool appearance.

Scarves and Wraps 

Women's scarf accessories oversized scarf blanket scarf infinity scarf

Chunky blanket scarf | knitted infinity scarf | Oversized square scarf

On days when you can’t bear to leave the comfort of your home, take that “still-in-bed” feeling with you. Large wool blanket scarves not only offer a ton of warmth, but they’re also really versatile. You can wrap it securely around your neck or simply drape it over your shoulders, depending on how cold it is. Faux-fur stoles and knitted infinity scarves tend to be more minimalistic in their appearance, making them chic finishing touches to elegant ensembles.


Women's glove accessories touchscreen gloves fur trim cuff gloves heat lined winter gloves

Casual gloves | heavy-duty winter gloves | evening winter gloves

Whether you’re going ice skating or headed to a winter formal, there are gloves designed for every occasion in order to prevent your fingers from turning into icicles. Many gloves have unique features based on your needs such as fleece or cashmere lining for extra warmth or touchscreen capabilities, allowing you to use your phone without taking them off.

Women's Clothing for Spring and SummerWomen's Clothing Buying Guide for Spring and Summer

For fresh outfits that carry you through the warm season, mix a few fun trend pieces with workhorse wardrobe staples.
How to Layer Clothes for FallHow to Layer Clothes for Fall

Learn how to layer clothes for fall with this step-by-step guide starting at your base and working up through sweaters, jackets, scarves, and accessories.