Cozy Winter Outfits You’ll Want to Live In All Season

Cozy and chic aren’t supposed to mix, but these outfits show they absolutely can. Yes, you read that correctly, you can wear one item and still look put-together. Like when you’re bundled up in your coziest sweatshirt, sauntering into the kitchen for coffee only to realize there’s a giant stain in the shape of the state of Ohio smack-dab in the middle. (I’m looking at you, Ohio-shaped coffee stain.) While it may not be technically possible to style an outfit around a stain, it’s 7:42 a.m. and you refuse to go back upstairs to change. Want to look cozy at the office minus looking like you rolled out of bed?

1. Chunky Cable Knit Sweater, Straight Leg Jeans, and Shearling Boots

There’s a reason I refer to chunky cable knit sweaters as the cozy sweater. Not only are they as toasty as clutching a steaming mug of hot cocoa, they also happen to look effortlessly chic, even when thrown on haphazardly like I snatched it right off of my kitchen chair (guilty…).

Keep things proportionate with a pair of straight leg jeans so you don’t look like a marshmallow, and accessorize with a slouchy tote and shearling lined boots. Make sure it’s roomy enough to accommodate the fact you’re definitely going to misplace a pair of gloves. Perfect for Saturday errands, coffee dates with your bestie and all of the 4:30 sunsets. Simply throw on whatever you can find (boots, jeans, a jacket, you name it) and leave the house. And hey, don’t beat yourself up over it.

2. Oversized Turtleneck Sweater Dress and Knee High Boots

An oversized sweater dress in a turtleneck style is the ultimate cold weather savior. Not only will it keep your arms and neck extra toasty, it’ll even save you the trouble of having to put together an outfit. Want to dress it up for an office lunch or a date night out? Simply cinch it with a skinny belt and throw on a pair of knee high boots. I know we’re all guilty.

3. Fleece Lined Leggings, Long Cardigan, and Fuzzy Slides

I’m not the only one who loves wearing leggings as pants, right? Fleece lined leggings. They look just like your typical pair of leggings on the outside, but on the inside, they’re practically acting as a space heater. Pair yours with a fitted tee and extra-long cardigan and you’re all set for working from home or spending hours at your favorite cafe. Just be sure to opt for sneakers instead of those adorable fuzzy slides you have your eye on so you can dodge any patchy ice in the parking lot.

4. Cream Fisherman Sweater and Wide Leg Corduroy Pants

That’s a win in my book. After all, isn’t that the point of dressing coquettishly? I’m not sure who designed the cream colored fisherman sweater, but I need to send them flowers. (Is it because I imagine a fisherman residing in a lighthouse hand-knitting it for his significant other?) Style yours with equally as cute wide leg pants (pro tip: opt for corduroy for an extra dose of coziness) and you’re all set for brunch with your effortlessly chic friend or aimlessly browsing in the bookshop.

The ribbed texture of the pants is the perfect complement to the sweater and prevents your IRL ensemble from looking one-note in pictures. Finish things off with loafers and a pair of thick socks and be prepared to field questions from friends and family members about whether or not you just returned from a cozy weekend at a cabin.

5. Puffer Vest, Waffle Knit Henley, and Joggers

The waffle knit henley keeps things extra toasty while the puffer vest warms up your core without the added bulkiness in the arms department (which makes reaching for objects in your car a whole lot easier). Go for joggers in a chic hue like oatmeal or charcoal. That way, you’ll be ready to tackle anything December has in store, from visits to the sledding hill and tree farm to cheering on your kiddo’s soccer team.

6. Sherpa Jacket, Ribbed Turtleneck, and Black Jeans

The garment practically oozes coziness. Want to elevate things a notch? Sherpa jackets are like getting cuddled up with a friendly sheep. And while I may seem unhinged for describing a favorite item of clothing of mine in such a manner, know that I consider this the highest of compliments. The sherpa material gives the jacket its oh-so cozy appeal while the tailored, jacket-y shape keeps it from looking too sweatsy. Underneath, a black turtleneck will keep your neck toasty while adding a clean line to your look. Round out your ensemble with a pair of Chelsea boots and coordinating beanie and you’re all set for a wander with your pup or catching up over mugs of steaming hot cider with your girlfriends.

7. Cashmere Crewneck, Satin Midi Skirt, and Ankle Boots

I rest my case. Just mimic this ensemble. This is your sign to get cute with cashmere. Pair a cozy crewneck in the material with a satin midi skirt and you’ll be ready to tackle anything December has in store, from company holiday parties to dinners with the in-laws.

8. Hoodie, Long Wool Coat, Leggings, and Chunky Sneakers

Instantly chic. Look, we all have days. Looking like you put in zero effort even when in actuality you’ve thought long and hard about your ensemble? Want to look like you rolled out of bed minus the, um, rolled out of bed aspect? And hey, it’s just as appropriate for days you have nowhere to be but want to look like you do.

I hate to be the bearer of bad fashion tidbits, but… the wool coat and hoodie duet may just be the cutest ensemble of the season. The tailored shape of the wool coat dresses everything up while the hoodie keeps your noggin (and ears!) warm should the December wind take a turn for the rude.

In short, it’s the perfect ensemble for trips to the coffee cart, school drop off, travels and basically anytime you want to look like you have it all together minus actually, um, having it all together. (Pro tip: go for a cream or gray colored hoodie to keep things cohesive.) Want to look like you cost money? Want to mimic the look?

9. Quilted Jacket, Cable Knit Sweater, and Riding Boots

Want to look like you have muck boots IRL? Start by teaming a lightweight quilted jacket with a cable knit sweater, pair of slim jeans (or, hey, even a pair of dark-colored leggings!), set of riding boots and plaid scarf. It’s the perfect ensemble for countryside strolls, farmers markets and, well, Target. (We’re looking at you, skinny jeans with tights, gal!)

10. Matching Knit Lounge Set and Long Puffer Coat

You can also dress up the bottom half of your ensemble by opting for a pair of jeans in lieu of sweatpants. (Well, you’ll also want to throw on a chic set of pants and turtleneck, but you get the idea.) Matching lounge sets are like wearing PJs outside, but, like, chic. And since the pants and top coordinate, no one will suspect you threw yours on at the crack of dawn IRL.

Start with a coordinating set in a sumptuous neutral shade (think: heather gray or camel) and heavier knit. Next, throw on a puffer coat, a set of hoops and a cute set of kicks and you’re all set to tackle errands, travels and lazy Sundays when the temperature outside dips below reasonable. It’s the perfect ensemble for chilly commutes and days when the forecast calls for anything less than reasonable.

11. Teddy Coat, Black Turtleneck, and Tailored Trousers

Just slip on a teddy coat and call it a day. Pair a ribbed turtleneck with tailored trousers to look polished for the office, a day at the museum, or a nice dinner out. The plush coat and structured pants duet ensures you look pulled together while the loafers and structured handbag ensure no one mistakes you for someone who isn’t headed to important meetings IRL.

12. Plaid Flannel Shirt, Thermal Tee, and Fleece Lined Jeans

For a more casual look, try layering an open plaid flannel over a thermal tee to create two layers of warmth. The fleece lined jeans are basically like wearing two pairs of denim at once. And while we’re not typically flannel fans, there’s something to be said for an extra layer come cozy cabin get togethers and backyard bonfires that leave you smelling of smoke for days. To recreate the look, team a pair of fleece lined jeans with a thermal tee, unbuttoned flannel, beanie and lug sole boots and, hey, you’re basically legally allowed to hack one log for IG.

13. Mock Neck Sweater, Faux Leather Leggings, and Long Cardigan

Faux leather leggings are the it-girl legging of the moment, and the sleek-but-glammy pair takes on an extra element of coziness when given a fleece lined twist. To recreate the look, team a pair with a mock neck sweater and long cardigan. (The mix of shiny and soft textures will ensure the all black ensemble still packs a punch.) (Pro tip: team everything with a delicate gold necklace that rests at the neckline and you’re golden.)

14. Wool Blend Shacket, Cropped Hoodie, and Wide Leg Jeans

A wool blend shacket, jeans and sneakers. Shirt or jacket? A wool blend shacket wants it to be both, and we’re not gonna lie, we love having another option come chilly coffee runs a-knocking. Opt for wide leg jeans to counter the shape and keep proportions in check. This is another easy layering equation: a boxy knit, cropped hoodie + wide leg jeans. Throw on loafers if you want to appear slightly more responsible or sneakers to keep the look casual. Throw on a pair of sneakers and a cap to lend the look a sporty edge.

A laid back but considered look that’s perfect for casual Fridays, running weekend errands, or catching up with friends (over a drink at that brewery that’s always freezing no matter the season). Chic without trying too hard.

15. Ribbed Knit Dress, Cropped Cardigan, and Fleece Lined Tights

Ribbed knit dresses are form flattering without being body hugging, and the winter friendly knit is more insulating than its woven counterparts. For even more warmth, layer with a cropped cardigan. Perfect for church, holiday parties, and days at the office where you want to look a tad more girly. Yes, you can wear a dress in the winter, especially when paired with fleece lined tights. Pair with loafers or knee high boots (depending on the weather), a cropped cardigan, and you’re all set for holiday parties, days at the office, church, etc.

16. Long Sweater Coat, Fitted Tee, and Leggings

The sweater coat is basically a cardigan that’s gone away to boarding school and come back confident. Chunkier, longer, and structured, it can take the place of a jacket on milder winter days. Pair it with a long sleeve fitted tee and leggings to stay toasty for hours on end. Great for running errands, working from a coffee shop, or holiday travel (bonus points because it can double as a blanket on the plane).

17. Puffer Jacket, Fleece Quarter Zip, and Snow Boots

Cold weather dressing doesn’t get any more practical than this. The insulating fleece quarter zip is perfect for layering and can easily be unzipped when you enter the inevitably too warm indoor environments. The puffer jacket is your best bet for braving the elements, and will work overtime if you’ll be out and about for any length of time (i.e. standing in a parade route, watching the kids sled, etc). For lower halves we recommend either warm leggings or lined jeans. A pom beanie and mitts will seal the deal, making you the coziest spectator in the bunch. If the weather report mentions the term wind chill, this is your outfit.

The sweater and puffer jacket combo is a surefire way to stay warm. The fleece lined puffer jacket protects you from the elements and the insulating quarter zip is perfect for layering. Swap in a pair of jeans if you’re feeling adventurous, but otherwise we suggest a pair of insulated leggings especially if you plan on braving the elements for any length of time, say if you’re planning on watching the kids sled for the better part of an hour.

Complete the look with either snow boots or a pair of lug soled boots if you’re feeling brave (they’re cuter than you think!). Not only will you stay toasty, but you’ll look the part too. Stylish, warm, and oh-so-ladylike, this is the perfect inclement weather uniform.

18. Slouchy Sweater, Silky Slip Skirt, and Sneakers

There’s something undeniably romantic about this look. We love the unexpected combo of a slouchy, oversized sweater with a silky slip skirt. Best dressed when the two pieces share a color story (think: champagne + oatmeal), and elevated with the addition of sneakers for a weekend brunch or errand running ensemble.

19. Turtleneck Bodysuit, High Rise Jeans, and Shearling Lined Clogs

We know, we know, tucking in your sweater is a lost cause. Enter the turtleneck bodysuit: the perfect layering piece to keep everything in its place, keep your neck toasty, and avoid the dreaded sweater bunch at the waist. Style with high rise jeans for a clean, put together look that you can add pretty much any jacket or coat over.

Perfect for coffee runs with the girls, lunch with your mom, or casual days at the office. Who needs a jacket when you have a sweater coat? Perfect for casual days at the office, coffee runs with the girls, lunch with your mom, etc.

20. Sweater Vest, Collared Shirt, Wide Leg Trousers, and Cropped Puffer

Channel your inner preppy/grandpa with this cold weather take on the sweater vest look. Layer it over a button up and style with wide leg trousers and loafers (pro tip: dress them up with a pair of patterned or colorful socks). The ultimate power couple: a puffer jacket + sweater vest. Opt for a cropped puffer to offset the wide silhouette of the pants. Channel your inner grandpa with this cozy sweater vest look. Chic and polished, but oh-so comfortable, we love that this look strikes the perfect balance. Try a pair of patterned or colorful socks to dress up your loafers.

21. Oversized Cardigan, White Tee, and Mom Jeans

You’ve earned it. It’s Friday and you deserve to wear something more comfortable than slacks. Think of the oversized cardigan as your adult version of a security blanket: it’s oh so cozy, dresses up a pair of mom jeans + a basic tee, and is the perfect layering piece to have by your side all winter long. Pro tip: button a couple of buttons at the front for definition at the waist.

22. Faux Fur Vest, Long Sleeve Thermal, and Leggings

Best dressed while staying cosiest. Who says you can’t dress up leggings? We love this take on leggings and a long sleeve thermal. Luxe and cozy, we adore the addition of a chic faux fur vest to dress up this otherwise sporty pairing. Pro tip: stick with neutral tones (like cream or chocolate) to avoid a costumey look. Pro tip: finish with a cross body bag + tall boots for added pizzazz.

23. Merino Wool Sweater, Wool Trousers, and Loafers

Style with a long coat and clean sneakers to really dress them up. When the office AC is cranked up to arctic levels (or your commute involves standing on a train platform), layer a cashmere sweater over a turtleneck and button up for maximum coziness. Chic and put together, we love this look as the perfect take on business casual, especially when paired with a long camel coat. There’s a reason merino wool is hailed as one of the best natural fibers out there: it’s lightweight, moisture-wicking, and oh so cozy. Style a merino wool sweater with a pair of wool trousers and a pair of loafers + merino socks for an oh so polished office ensemble.

24. Fleece Pullover, Corduroy Skirt, and Tall Boots

We’re not even a little bit bitter that we didn’t think of this first. Tucking your fleece pullover into a corduroy skirt is such a chic take on this classic outdoor layering piece. Pro tip: opt for a neutral colored pullover (like cream or brown) so that it looks more intentional (otherwise you risk looking like you hopped off a trail and into a bakery). It’s like a sweater weather but make it for your legs: think of corduroy pants as sweater weather for your lower half. Pro tip: swap out pants for a skirt for an unexpected twist.

25. Knit Joggers, Oversized Sweatshirt, and Long Wool Coat

We suggest trading them in for a pair of knit joggers. Chic and cozy, we love that they’re the perfect alternative to sweats (pro tip: opt for a set for a more put together look). Pro tip: for a chic monochromatic look, opt for pieces in complementary shades (think: cream + camel).

26. Plaid Blanket Scarf, Black Sweater, and Leather Leggings

Think of the plaid blanket scarf as the perfect take on layering: oh so cozy, we love pairing one with a leather jacket + slouchy knit sweater. It’s chic yet practical (when the sun sets, you’ll be glad you have a blanket at hand!). Pro tip: opt for jewel toned plaids (think: forest green, burgundy) to really warm up your ensemble. Pair this look with black ankle boots and a crossbody bag and you’re set for anything below 40 degrees with your dignity intact.

27. Cable Knit Sweater Set, Wool Coat, and Fur Lined Boots

You’ve officially levelled up. Time to tackle the final boss of sweater weather: matching cable knit sweaters + pants. Chic and oh so cozy, we love this elevated take on sweats, especially when styled with a chic beanie and luxe longline coat. Think of this look as a knit jogger set, but dressier: we love styling knit lounge pants with a slouchy crewneck sweater. Chic yet cozy, it’s the perfect formula for errand runs, airport outfits, or any and all cozy Sunday activities.