Winter Layering Outfits That Keep You Warm Outside Without Melting the Second You Walk Indoors

From cozy weekend looks to work-appropriate winter layering ideas (and some that we’re oddly excited to wear), these outfits will make it easy to look chic at any temperature. Layers.

1. Turtleneck, Crewneck Sweater, and Wool Coat

Pairing a crewneck sweater with a thin turtleneck underneath is a perfect winter layering combo. Your neck will thank you for keeping it warm! The turtleneck layer helps to keep sweaters from feeling itchy against your skin and adds warmth without looking bulky so your sweater falls properly. Perfect for work, running errands, or heading to a restaurant that has a door that opens directly onto a wind tunnel. Style with a camel colored wool coat, jeans, and a nicely tucked turtleneck collar (intentionally, not accidentally).

2. Button-Down Shirt Under a Cable Knit Sweater

You know that outfit with the vibe of library card and strong opinion about tea? Channel that energy in these pieces and roll both sleeves up once so the cuffs peek out. Try layering a collared shirt underneath your favourite chunky cable knit for an easy way to elevate your look! It’s the perfect look for when you want to seem pulled together, but are adamantly not wearing anything that needs to be ironed beyond the collar. Pair with loafers, wool socks, and straight leg trousers, and leave a little hem exposed.

3. Thermal Henley, Flannel Shirt, and Puffer Vest

For chilly but potentially sunny days (you know, like every winter day), layer pieces that will work individually, so you can take things off as the weather changes throughout the day. Pair a thermal henley with an open flannel for warmth and added color and texture. The puffer vest will keep your core warm and arms free. This look will be especially welcome at Christmas tree farms, pumpkin patch leftovers, and on Saturday mornings at the hardware store. (When you don’t buy a sixth flannel shirt.) Pair this layered look with boots and jeans cut slim.

4. Fitted Bodysuit, Oversized Cardigan, and Long Coat

A bodysuit is so underrated as a winter layering piece. Nothing gets untucked when you’re reaching for something on a high shelf, and a cream or black colorway can be incorporated into pretty much any cardigan color. A smooth base lets an oversized cardigan look slouchy on purpose rather than swallowing you whole. Ah yes, winter shopping. Drafty work building? Holiday shopping that involves removing said layers throughout multiple establishments? We recommend pairing this look with boots (to combat slush), a long wool coat, and belting the cardigan (loosely).

5. Sweater Vest Over a Long Sleeve Tee

If you’re anything like us, you’re still not sold on sweater vests (for us, it always reminds us of one particularly memorable substitute teacher). Layered over a fitted long sleeve tee, sweater vests provide warmth in all the right places (and leave the arms free to roam). Pro tip: They also take up less room in your coat sleeve than a second full sweater. Whether you’re wearing wide leg trousers to work or jeans for a casual lunch, it looks fresh. Pair with a wool blazer when it dips below polite outside. Colorways like charcoal and oatmeal will be the most versatile.

6. Blazer Over a Hoodie With a Wool Overcoat

Business on top, nap time underneath. Yes please. Basically, this is the closest thing to wearing a blanket to work and not getting in trouble. The hoodie softens the structure of the blazer and makes for a more casual look overall. Optimal for casual Fridays, days of back to back meetings (with a trip to the grocery store in between), and of course, travel days. But hear us out. Make sure that your hoodie hood is tucked under the collar of your blazer and add a long overcoat and white sneakers or loafers (the chunkier the better) to keep it looking current, not confused.

7. Mock Neck Top, Shacket, and Straight Leg Jeans

The shacket: A garment that is neither a jacket or a shirt, but thrives on being both. In colder temps, layer over a fitted mock neck and under a parka. On milder winter days, wear it on its own. Plaid shackets add just enough pattern to keep things from getting too sleepy, while leather ankle boots and straight leg jeans keep things grounded.

8. Slip Dress Over a Turtleneck With Tights

Emerald. Burgundy. A rich, deep color like these two makes a slip dress winter ready. Layered over a fitted turtleneck, paired with opaque black tights, your slip dress (currently sulking in your closet since September) can have a second act. A formulaic option for date night, holiday parties, and events that call for something dressier than jeans, but not cocktail dress level energy. Throw on a tailored coat and knee high boots and you’ll appear as though you’ve had it all figured out all along.

9. Quarter Zip Pullover Over a Collared Shirt

The quarter zip may seem like weekend golf attire, but layered over a collared shirt, it’s ready for the city. The collar prevents wind from entering, and the quarter zip makes it easy to adjust your warmth level with one hand (in case the office thermostat is an unresolved issue). Brunch, travel days (involving planes and cold sidewalks), and work approved. Or for a sporty (but not quite gym clothes) look, try pairing with tailored trousers or dark denim and a quilted jacket and leather sneakers.

10. Long Sleeve Tee, Denim Jacket, and Teddy Coat

Wearing a denim jacket under a coat sounds like a lot of jacket, and that is exactly why it works. The key to pulling this look off: Invest in a slightly larger sized coat, so that there is room for your denim underneath (no stuffed sausage situation here). Teddy coats are extra huggable, and denim jackets add an edgy yet structured vibe. Start with basics underneath (white long sleeve tee, black jeans, chunky boots), and layer on from there. Perfect for errand-filled days, trips to the market (involves standing outside longer than you’d like), or just a casual weekend look.

11. Fair Isle Sweater, Thermal Leggings, and Shearling Boots

Snow angels optional. Channel your favorite holiday movie cabin (you know the one we’re talking about). Pair fleece lined leggings (for maximum coziness on sledding afternoons and walks in the snow) with a Fair Isle sweater. Let the pattern do the heavy lifting. Slip on shearling lined boots and a puffer coat, then add a knit beanie in a color pulled from the sweater pattern so everything feels tied together.

12. Silk Blouse, Cardigan, and Wide Leg Trousers

Paired with a cardigan, a silk blouse would be just practical enough for commuting in winter. When you’re ready to shed the sweater at the office (because you’re going to feel toasty, trust), you can remove it and still look office presentation appropriate. The peek of silk at the collar and cuffs adds a soft and luxe element to the look. Holiday events, client lunches, and any occasion calling for business casual. Pro tip: Make sure the cardigan is buttoned, the blouse is tucked into wide leg, high waisted trousers, and you’re wearing either pointed flats or low block heels to keep things polished.

13. Hoodie Under a Long Puffer Coat

Hoodie + Puffer Coat: This is the most utilitarian of our looks, but also the cutest, making it our favorite. Opt for a thicker fleece hoodie that you can count on to do some real insulating work and pair it with a long puffer coat. You can wear the hoodie inside or outside of the coat collar (the latter is cuter and also toasty since the hood will add some extra warmth around your face). This is a great outfit to throw on for running errands like dropping the kids off at school, taking the dog out for a walk, getting on an early morning flight, etc. Pair it with leggings or joggers and clean white sneakers to avoid a rumpled look, instead you’ll look relaxed!

14. Ribbed Tank, Chunky Cardigan, and Faux Leather Pants

Tank + Cardigan + Coat: Yes, it’s a tank. You just have to wear a cardigan substantial enough to serve as a coat, which will keep you cozy on short walks between indoor appointments. Wind resistance from the faux leather pants and a little edge. Warmth from the chunky cardigan. A light base from the ribbed tank. Bonus points if you belt your coat too. Top it off with a chic wool coat and you’re set. Add heeled ankle boots to lengthen your legs, and consider throwing on a chunkier gold necklace to fill out the neckline. We predict you’ll reach for this look for nights out with friends that include dinner and drinks, concerts, etc., basically anywhere indoors where you’ll be warm and toasty while everyone else around you is freezing.

15. Turtleneck Sweater Dress, Long Cardigan, and Knee Boots

Sweater Dress + Coat: If sweaters are basically fancy sweatshirts, then sweater dresses are the equally comfy-but-cute pajamas we can take out in public. Try on a few and find one that feels luxe and substantial and skims (rather than skimps) over your body. Try a long cardigan over your turtleneck sweater dress for additional layering that won’t interrupt that long, cozy line. Style it with knee high boots (try a pair of brown suede or black leather), fleece lined tights, and your favorite wool coat. A skinny belt at the waist helps prevent you from looking like a fuzzy rectangle. This look will get so much use come winter, from Thanksgiving leftovers season to office parties to church to cozy dates.

16. Flannel Shirt Tied Over a Sweater With Jeans

Crewneck Sweater + Flannel: Think of the flannel as a scarf you can tie a bunch of different ways! It adds an element of color and pattern, plus you can always wrap it snug around you when you step outside and it’s chilly. (It’ll also strategically conceal that one coffee splat you got on your sweater.) For this cute crewneck sweater outfit, opt for a sweater in a luxe color (black, cream, gray, camel, navy, etc.) that pairs easily with whatever flannel you choose. Then wear it on casual winter days, think going to see the holiday lights with friends, running an errand like grabbing a coffee, going on a road trip, etc. Bonus points if your friend’s car smells like snacks! For the rest, keep it simple: straight jeans and lace up boots, and consider a corduroy jacket if it’s looking like it’ll get serious this afternoon.

17. Knit Polo, Blazer, and Tailored Coat

A knit polo (think of it as the sweater’s more put-together sister) is perfect under a blazer. Try to find a polo made from a thinner knit so it’ll sit nicely under your blazer without making the lapels stick out. The collar adds just the right amount of structure, while the knit polo keeps things from looking too office-appropriate. Wear this look on days when you have back-to-back meetings, for job interviews, or even out to dinner. Save this look for chiller Fridays at the office, running weekend errands, etc. Straight-leg gray or camel-colored pants are best here. Top them off with a tailored coat and leather loafers. Sweater + Blazer: This one’s for all the women who love old money style but don’t have an old money (read: trust) fund. No, we’re not crazy.

18. Waffle Knit Top, Quilted Jacket, and Corduroy Pants

Fun fact: Corduroy pants also help to shield you from chilly winds, which is an added bonus! The windproof quilted jacket and lightweight waffle knit base layer provides warmth without bulk. Corduroy Pants + Sweater: For a cozy (in more ways than one) winter look, reach for a pair of corduroys. They add instant coziness and texture to an OOTD, plus they have a slightly vintage vibe to them that pairs perfectly with chunky sweaters this season. Try them in different colors (olive, rust, brown, etc.) that can pair with different sweaters, and style them with a pair of suede boots. We promise you’ll look like you just found the cutest antique shop in town.

19. Crop Sweater Over a Collared Dress

Dress + Cropped Sweater: Here’s another easy way to look put together with minimal effort: Just throw on a dress and then layer a cropped sweater on top. The collar of the dress adds visual interest at the neckline and the cropped sweater skims over your waist for the perfect fit. We recommend trying this with both mini and midi dresses, but just make sure to find a sweater that hits at your natural waistline. This outfit will come in clutch on winter days when you want to wear a dress, but don’t want to sacrifice coziness, think brunch dates, taking holiday pics with friends and family, even on chiller Fridays at the office. P.S. Pair them with Mary Janes or loafers and sheer black tights, and add a peacoat or cropped wool jacket.

20. Leggings, Long Tunic Sweater, and Parka

The latter will make you feel seriously fancy while the former will keep you extra toasty when you step outside. The extended hem of the sweater will ensure you stay covered up even if you opt for a shorter parka. Opt for a long tunic sweater, for full coverage, and pair it with some chunky leggings to keep the chill away. Finish the look with a pair of waterproof boots so you’re prepared for any slush puddles standing in your way. Wear this winter OOTD on days when you’re running errands, traveling, or otherwise out and about all day and don’t want to give much (if any!) thought to getting dressed.

21. Plaid Blanket Scarf, Black Turtleneck, and Camel Coat

A blanket scarf is the easiest way to add a full layer of warmth in five seconds, and it hides a multitude of wardrobe sins. Try tying one around your shoulders and let the ends drape in front or in back. Turtleneck + Scarf + Coat: Here are two easy ways to wear this plaid scarf this winter: Wrap it snugly around your neck or drape it over your shoulders. Pair the scarf with a camel coat, black turtleneck, black jeans, and Chelsea boots (preferably leather) to look like you just stepped out of a Pinterest board. Save this look for days when you’re headed to an outdoor winter/holiday market, on your way in to the office, out for an afternoon walk, etc. This scarf would also make the perfect lap blanket on a long train ride. Consider that a bonus feature.

22. Graphic Sweatshirt, Leather Jacket, and Long Coat

There is something very cool about a vintage style sweatshirt layered under a leather jacket, like you might be in a band but also have your taxes done. Sweatshirt + Leather Jacket + Long Coat: This winter OOTD screams sleek. The sweatshirt adds an element of comfort while the leather jacket ups the edginess (and also helps protect you from any chilly winter gusts), and the long coat makes it winter appropriate. Try wearing straight leg jeans and combat boots with this look, and opt for a sweatshirt that’s long enough to slightly extend beyond the hem of your leather jacket. Save this look for casual Fridays at the office, going out to dinner with friends on the weekend, heading to a concert, etc.

23. Ribbed Knit Set Under a Wool Wrap Coat

Knit Top + Pants Set: Knit sets are basically like a cheat code for looking fashionable with virtually zero effort. Thanks to the lightweight set-up, the coat does the heavy lifting, so it doesn’t feel bulky. Try wearing a matching set made up of a ribbed knit top and pants underneath a chic wrap style wool coat. The monochromatic look will make your OOTD appear polished while creating a streamlined silhouette. Opt for neutral colorways (think: cream, oatmeal, etc.) for extra points and finish the look with either leather sneakers or chic ankle/over-the knee boots. Save this winter look for traveling, WFH days when you’ve got plans to meet friends for dinner later, holiday get togethers, etc.

24. Fleece Pullover, Thermal Tee, and Insulated Pants

Fleece Pullover + Thermal Tee + Insulated Pants: Okay so this OOTD is not here to impress, it’s here to keep you as warm as humanly possible. Insulated pants will shield your legs from chilly temps, the fleece will trap in heat, and the thermal tee (which you should absolutely reach for any time the temps dip this winter) will wick away any excess moisture if/when you start to get a little toasty. Save this OOTD for braving the elements on snowy days, taking a hike this winter, attending an outdoor (read: frigid) soccer game, etc. Add warm socks and snow boots under a waterproof shell or puffer and you won’t be spotted shivering when the second half kicks off.

25. Cashmere Sweater, Faux Fur Vest, and Dark Jeans

Sweater + Faux Fur Vest: Cashmere sweaters are the softest, comfiest sweaters on the planet, so of course you’re going to want to reach for one on the chillest of days this winter. Simply pair yours with a chic faux fur vest and you’re all set! Not only will this combo add extra coziness and dimension to your winter OOTDs, it will also free up your arms so you can move them freely (and show off that gorgeous sweater sleeve). We suggest reserving this look for running into town to go winter/holiday shopping, going out for a festive lunch with friends, visiting the in-laws (they WILL ask you where you got the vest), etc. To ensure your outfit is cohesive from head to toe, wear dark wash jeans along with knee high boots. You can also include leather gloves for a complete look.

Wardrobe Staples From This Post

The pieces that repeat across these outfits.

• CUSHIONAIRE Leather Penny Loafers. Real leather that breaks in instead of breaking down.
• Amazon Essentials Low Heel Ankle Boots. A low block heel you can walk in all day, with a side zip.
• Mulberry Silk Square Scarf. Tie it at the neck, on a bag strap, or in your hair.