How to Dress for Freezing Weather and Still Look Cute
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Winter outfits for cold weather have two jobs, keeping you warm and still looking cute. The trick is layering pieces that are actually made for the cold, like down fill, shearling, fleece linings, and real wool. Every item below lists only the warmth features its maker states, so you know exactly what you are getting.
We pulled together 23 pieces from Everlane, Quince, Jenni Kayne, Barbour, Gap, Skims, Zappos, and more. The list starts with coats, moves through knits and base layers, and ends with boots and the small accessories that keep your fingers and ears happy. Mix and match them by number and you can build a whole week of warm outfits from one list.
1. Everlane Italian Belted Overcoat in Taupe Herringbone
Start with a long wool coat, because it does more for your warmth and your look than any other single piece. Everlane made this heavyweight style from a recycled wool blend milled in Italy, with a herringbone pattern, a nubby boucle finish, and a hem that hits below the knees. A tie belt cinches the waist so you still have some shape under all that wool.
Belt it over the oatmeal Quince fisherman turtleneck and the black Banana Republic flannel flares for an easy office outfit. On weekends, swap in the dark Citizens of Humanity jeans and the rustic brown Blundstones. Finish with the tartan Quince scarf tucked into the collar.
2. Everlane The Long Puffer in Navy
For the truly bitter days, you want a puffer with real length. Everlane fills this long navy style with recycled down insulation to keep you extra warm. Navy also reads a little softer than black, so it looks more polished on the way to work.
Wear it over the Skims fair isle base layers and the felted Jenni Kayne Chalet Pant when you are running errands in the snow. The Sorel Joan of Arctic boots and the camel UGG mittens make it ready for a real storm. Pull on the Everlane beanie and you are set for a long, cold walk.
3. Jenni Kayne Shearling Aurora Coat in Camel
Shearling is one of the coziest things you can wear, and the Aurora Coat gives you two looks in one. It is fully reversible, with plush shearling on one side and sleek leather on the other. Even the pockets flip to match whichever side you wear out.
Wear the shearling side out over the ivory cocoon cardigan and straight jeans for a soft camel and cream outfit. Flip it to the leather side for dinner with the black turtleneck and the flannel flares. Brown leather gloves and the UGG Ultra Minis keep the whole palette warm.
4. Barbour Beadnell Polarquilt Jacket in Olive
Barbour calls this take on its iconic Beadnell a luxuriously warm jacket, and the details back that up. It pairs a diamond quilted outer with a super soft fleece lining and handwarmer pockets. A contrast cord collar keeps the classic country look.
Layer it over the oatmeal fisherman turtleneck with dark straight jeans and Blundstones for a weekend away. The cable knit Smartwool socks peeking over the boots look great with olive. Add the neutral tartan scarf for a cozy British feel.
5. Gap Sherpa-Lined Shawl Denim Jacket in Light Wash
Most jean jackets are too thin for January, but a sherpa lining changes that. Gap lines this oversized style through the body and adds a big sherpa shawl collar that sits right around your neck. The denim is authentic non-stretch, so it looks like a true classic jean jacket.
Throw it on over the black Luxe Rib Turtleneck with the black flannel flares for a fun mix of casual and sharp. It also layers easily over the Skims half zip on a lazy weekend. The sherpa shoulder bag and UGG Ultra Minis keep the cozy theme going.
6. Athleta In the Clouds Jacket in Sahara
High pile fleece is the cozy layer you will reach for all season long. Athleta made this jacket from boucle fleece with plush warmth, plus large hand pockets with a soft brushed lining. It was designed for the commute and weekend travel, so it looks neat enough to wear out.
Wear it over the Skims half zip and leggings for a warm, sporty outfit. On the coldest days, add the long navy puffer on top. Smartwool socks and Sorel boots finish the look for snowy mornings.
7. Quince Mongolian Cashmere Fisherman Turtleneck Sweater in Oatmeal
Chunky knits do a lot of the heavy lifting in winter, and this one is Grade A Mongolian cashmere. Quince knits it in a denser, more substantial weight with a classic ribbed fisherman stitch. The slouchy fit and tall neck make it feel like wearing a soft blanket.
Tuck the front into the Banana Republic flannel flares and add the Everlane overcoat for a polished look. It is just as good with straight jeans and Blundstones on a Saturday. The chocolate leather gloves pick up its warm tones.
8. Jenni Kayne Cashmere Cocoon Cardigan in Ivory
Some days call for a sweater you can wrap around yourself, and this cardigan is exactly that. It is 100% Mongolian cashmere in a midweight knit with a dramatically oversized, relaxed shape. Faux horn buttons give it a little polish.
Button it over the black turtleneck with the charcoal Chalet Pant for a soft weekend outfit. It also works as a cozy middle layer under the shearling coat on very cold days. Add the UGG Ultra Minis and a knit beanie for a cute walk to the coffee shop.
9. Everlane The Luxe Rib Turtleneck in Black
Every cold weather outfit needs a thin, fitted turtleneck underneath. Everlane makes this one from fine ribbed Supima cotton with stretchy elastane, so the snug fit still feels comfortable. The brand even suggests wearing it under a sweater for extra warmth.
Slip it under the ivory cardigan or the sherpa denim jacket to keep your neck covered. It looks sleek under the leather side of the Jenni Kayne coat with the black flannel flares. Gold earrings and the Quince gloves are all you need to finish.
10. Skims First Layers Half Zip Long Sleeve in Obsidian Winter Fair Isle
Staying warm without looking bulky starts with a good base layer. Skims made this half zip as an essential base layer meant to keep you cozy and dry. The fair isle print makes it cute enough to show off when the coat comes off.
Wear it with the matching First Layers Legging under the long puffer for sledding or a ski weekend. Under the In the Clouds Jacket, it makes a fun outfit for a winter hike. The Everlane beanie and UGG mittens suit the alpine feel.
11. Skims First Layers Legging in Obsidian Winter Fair Isle
Leggings made for layering make a huge difference when the wind cuts right through your pants. Skims describes this fair isle legging as an essential for winter warmth, made to build your cold weather look from the inside out. The black and gray print looks fun on its own with a long sweater.
Pair it with the half zip as a full set under the Everlane puffer. It also slips under the straight jeans on the coldest days. Add the Smartwool socks and Sorel boots for a snow day outfit.
12. Banana Republic High-Rise Flare Italian Flannel Pant in Black
Office outfits need warm pants too, and flannel is the answer. Banana Republic cut this high rise flare from a warm Italian wool blend flannel, with fabric from the mill Manifattura Emmetex. A twisted seam wraps the outseam forward to make your legs look longer.
Pair them with the fisherman turtleneck and the Everlane overcoat for a classic workday outfit. For dinner, try the black turtleneck and the leather side of the Jenni Kayne coat. The Blundstones peek out nicely under the wide leg on snowy commutes.
13. Jenni Kayne Chalet Pant in Charcoal
When you want the comfort of sweatpants with a much nicer look, the Chalet Pant is the one. Jenni Kayne made it from a soft felted wool blend with a touch of stretch, designed for warmth. An elastic waist, an adjustable drawstring, and a straight leg keep it easy to wear.
Wear it with the ivory cashmere cardigan and the black turtleneck for a cozy day at home or on the road. Add the long navy puffer and Blundstones when you head out. The tartan scarf brings a little pattern to all that gray.
14. Citizens of Humanity Zurie Straight in Helia
Straight jeans are the easiest base for winter outfits, and a dark wash looks especially sharp with heavy knits. The Zurie has a high rise and a clean straight leg in soft comfort stretch denim. Helia is a dark indigo wash, and the brand says the fit runs true to size.
Tuck the hems into the Sorel boots on snowy days or let them fall over the Blundstones when it is just cold. They look great with the oatmeal turtleneck and the Barbour jacket. On frigid mornings, wear the Skims leggings underneath for extra warmth.
15. Blundstone Women's Thermal #584 in Rustic Brown
Blundstone took its classic Chelsea boot and made it ready for winter. The Thermal has waterproof leather, a Thinsulate lining, and a sheepswool lined footbed. Rustic brown leather goes with almost everything on this list.
Wear them with the straight jeans and the Barbour Polarquilt for an outdoorsy weekend look. They also work under the flannel flares on a snowy commute. Let the Smartwool cable socks peek over the top for a cozy touch.
16. Sorel Joan of Arctic Waterproof Boot in Black/Quarry
Real snow on the ground calls for the Joan of Arctic. It has a waterproof leather and suede upper, seam sealed construction, a waterproof rubber shell, and a removable felt inner boot. Faux fur trim at the collar adds warmth and a cute, cozy finish.
Pair them with the Skims leggings and the long navy puffer for a full snow day outfit. Straight jeans tucked in with the Athleta fleece on top work well too. Add Smartwool socks inside and the UGG mittens on your hands.
17. UGG Classic Ultra Mini Boot in Chestnut
Short and easy to slip on, the Ultra Mini is a cozy pick for cold errands. Its upper is water repellent Twinface sheepskin with 17mm sheepskin linings, and the footbed is lined with a wool blend UGGplush. A Treadlite outsole adds traction and cushioning.
Wear them with the ivory cardigan and the Chalet Pant for a soft weekend look. With the Skims leggings and the sherpa denim jacket, they make a cute, casual outfit. The sherpa shoulder bag matches the cozy mood.
18. Smartwool Everyday Cable Crew Socks in Fossil
Warm feet make the whole outfit feel better, and good wool socks are an easy fix. These Smartwool crews are a 74% Merino wool blend that the brand says offers long lasting warmth. The slim fit cuts bulk inside boots, and the toe is nearly seamless.
Pull them up over the Skims leggings inside the Sorel boots. The cable knit looks cute peeking over the Blundstones with cuffed jeans. The fossil color blends right in with the oatmeal sweater and the taupe beanie.
19. Everlane Chunky Ribbed Beanie in Taupe Melange
Nothing tops off a winter outfit like a thick knit beanie. Everlane knit this one in a wide, chunky rib with a tall folded cuff to keep it snug. It is a blend of hemp and RWS certified wool.
Wear it with the long puffer and the Skims set for a ski lodge feel. It looks just as good with the Barbour jacket and the tartan scarf. Match it with the cable socks for a tonal look.
20. Quince Mongolian Cashmere Tartan Scarf in Neutral Tartan
Wrap on a plaid scarf and a plain coat suddenly looks styled. Quince made this one from 100% Grade A Mongolian cashmere in a classic tartan. The neutral colors go with camel, olive, navy, and black coats.
Loop it twice around the collar of the Everlane overcoat or the Barbour jacket. It adds pattern to an all charcoal outfit built on the Chalet Pant. The chocolate gloves and a cozy beanie pull out its warm tones.
21. Quince Cashmere Lined Leather Gloves in Chocolate
Leather gloves look more grown up than knit ones, and these are lined for real warmth. Quince uses sleek lambskin leather with a soft cashmere lining. Chocolate brown feels softer than black and works with every coat here.
Pair them with the overcoat and the flannel flares for work. They look great with the camel shearling coat as well. Keep the UGG mittens for the really frigid days and these for everyday wear.
22. UGG Chunky Rib Mitten in Camel
Mittens keep your fingers together, which is why so many people find them warmer than gloves. UGG knits these in a soft chunky rib made for long lasting warmth, with a small leather logo clamp. The camel shade looks sweet with brown boots and cream knits.
Wear them with the long puffer and Sorel boots on snow days. They also look cute with the Athleta fleece and UGG Ultra Minis. Add the beanie for a matching knit set.
23. Gap Small Sherpa Shoulder Bag in Ivory Beige Frost
Fuzzy textures make winter outfits fun, and this little bag is pure fluff. Gap made it in soft sherpa with a vegan suede handle, a removable shoulder strap, and a magnetic closure. You can carry it by hand, at the elbow, crossbody, or over the shoulder.
Carry it with the sherpa denim jacket and the UGG Ultra Minis for a cozy matching look. It also softens a sharp outfit like the overcoat with the flannel flares. Wear it crossbody with the Athleta fleece when you need your hands free.
What should I wear in really cold weather to stay warm but still look cute?
Start with a thin base layer like the Skims half zip and leggings, then add a cashmere or chunky knit. Top it with a coat that has real insulation, such as the down filled Everlane puffer or the reversible shearling Jenni Kayne coat. Finish with lined boots, a beanie, and gloves so nothing is left out in the wind.
Which boots work best with winter outfits for cold weather?
For deep snow, the Sorel Joan of Arctic has a waterproof shell and a removable felt inner boot. For cold, wet sidewalks, the Blundstone Thermal has waterproof leather and a Thinsulate lining. The UGG Ultra Mini is the cozy pick for dry, cold days.
How do I layer for winter without looking bulky?
Keep the layers closest to your body thin and fitted, like the Luxe Rib Turtleneck or the Skims base layers. Save the volume for one piece, either a chunky sweater or a puffy coat, not both. Slim wool socks like the Smartwool crews also keep your boots from feeling tight.
