19 Winter Outfit Ideas That Will Make Your Basic Sweaters Look Brand-New

Anyone who's resided in a cold climate can tell you that excitement about winter isn't always rooted in reality. Sure, buying our little winter coats or breaking in new boots is cute, but when temperatures drop below freezing? All bets are off. Realists can attest that looking chic when it's cold outside is challenging. Even more so when our desire to get dressed up can be easily deterred by a myriad of factors—e.g., the forecast for the day or staples that feel as dull as the winter sky. Basically, catching a case of the winter blues in the wardrobe department is as inevitable as an oncoming cold front. However, not all hope is lost! There are a few ways to combat the mid-winter dressing slump, starting with your sweaters.
Hear us out: knitwear is the most significant part of any winter wardrobe on a functional level but also for fashion purposes. How you style this staple can either make you want to slump back into bed or can help you shake off any gloom swiftly. If you're more interested in the latter, you'll want to keep reading as we're sharing some game-changing sweater styling tips. Ahead, you'll find 19 winter outfit ideas to showcase different ways to style knitwear for various occasions, climates, and sartorial perspectives. If these styling hacks can't get you out of your winter slump, nothing will.
Layers are the key to bringing the turtleneck in the back of your closet back to life. Use your sweater as a base layer, then add a button-down shirt, long coat, trousers, and structured bag for a look that will liven up your winter work uniform.
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When winter temperatures are bleak, layering is the best way to make it more bearable. In order to make your trusted crew-neck even cozier, try layering it with a T-shirt, contrasting cardigan, wool coat, and long scarf. Finish off the look with leather trousers if you need a little extra warmth.
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Your future self will thank you for investing in a solid scarf.
While warmth is one of the top priorities when choosing what to wear to work in the winter, that doesn't negate the importance of style itself. After all, you don't want to look like you rolled out of bed to get to the office! The best way to meld function and fashion is by adding one to two trendy items to your winter work uniform—e.g., a colorful cardigan or a buzzy handbag.
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Are you more interested in your winter wardrobe looking timeless over trendy? Well, you'll want to take note of the outfit above. While trousers and turtlenecks are already classic, they can become even chicer by merely being paired with a tweed jacket, kitten heels, and a structured handbag.
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One of the easiest ways to look chic during the wintertime is to make your accessories the focal point of your outfit. When in doubt, even the most "vanilla" staples can feel spicy when you add statement outerwear and accessories into the mix—e.g., the all-black outfit above shines with the addition of a white maxi coat and metallic clutch bag.
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Add a shiny new feeling to your monochrome winter outfits with a metallic handbag.
One more way to look polished during the winter is by leaning into preppy-inspired pieces that feel Princess Diana-coded. Try layering a long wool coat over two contrasting sweaters with skinny jeans, knee-high boots, and a baseball cap. It's a winter outfit formula that will make you look as posh as a princess.
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You can also shop this coat in brown, black, or gray if the navy version doesn't suit your taste.
If you're less interested in looking like you live in a palace but do want to give off the vibe that you own a ski chalet, then the outfit above is right up your alley. Pairing a shearling coat over a chocolate brown crew-neck sweater with wide-leg jeans, ankle boots, and a woven bag is a surefire way to look the part.
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I can personally attest to these jeans being ultra-flattering.
We've all had those days when you wake up on an ultra-cold winter day without wanting to dress up—enter the ensemble above. Nothing is easier to throw on than an oversize turtleneck with a matching maxi skirt when you can't be bothered. But should you want to make it look like you put in more effort getting dressed than you actually did, finish off the look with sparkly ballet flats and a woven shoulder bag.
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Let's just say you'll catch a few glances with these ballet flats.
Whoever said you can't look cool when it is cold outside never saw the outfit above. By pairing your warmest crew-neck sweater with thermal leggings, a long coat, moto boots, and a balaclava, you'll look edgy without being on the edge of hypothermia.
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Consider this your sign to swap out your winter boots for something a bit more trend-forward.
You never have to choose between being freezing or looking fashionable—case in point: the outfit above. Nothing will take the chill off better than a faux fur coat styled with a turtleneck sweater, wide-leg jeans, and ankle boots. It's an outfit formula that's equal parts polished and pragmatic.
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You don't have to be a mob wife in order to make this purchase.
The side-slit at the hem of these jeans will allow you to show off your favorite ankle boots.
For those who reside in warmer climates, it can be just as challenging to figure out what to wear during the winter. Rather than opting for a heavy coat, try layering a light T-shirt underneath a knitted polo with a wool maxi skirt and pumps. It's a look that will keep you warm without overheating.
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Opting for a cashmere sweater is also a simple way to feel like your closet is a bit chicer.
What's another fail-proof formula fit for milder winter temperatures? See the outfit above for guidance. The key to navigating dressing for those 60ºF days is all about opting for lightweight layers—e.g., a leather blazer layered over an argyle print sweater or fishnet tights underneath a miniskirt.
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Although it might seem like you must pack away pieces commonly associated with "warm weather," that's far from the truth. Great knitwear can make any item winterized; reference the look above as proof. While most wouldn't dare to wear a pleated mini when it's cold out, it becomes a legitimate option when styled with an oversize turtleneck, leather bomber jacket, and chunky lug-sole knee-high boots.
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I'm sharing this in case you're in desperate need of a new white sweater.
Not exactly keen on wearing a miniskirt in the middle of winter? Try a maxi instead. Opting for a skirt made from heavier materials or a long hemline that can cover up thermal underpinnings will ensure its wearability in the winter. And if you're still unsure how to style the skirt, take inspiration from above by pairing it with a matching crew-neck sweater and contrasting accessories.
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If you're worried about your feet being cold, just add socks!
Rather than trying to winterize skirts, you can forego them altogether in lieu of an item that always works: leather trousers. Similar to the sweater, this staple is a quintessential part of any stylish person's winter wardrobe—therefore, it only makes sense to style them together! Even if you pair them with footwear that's not winter-friendly, you'll be rest assured this pairing will serve you well all season.
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When things begin to thaw out in the coming months, you'll want a way to wear your sweaters without breaking a sweat—enter the ensemble above. By pairing a turtleneck with an oversize blazer, leather shorts, and ankle boots, you'll be able to weather the remaining weeks of winter in style.
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You can wear these shorts well into the spring.
When navigating the transition from winter to spring, there's no better item to turn to than the cropped knit. Hear us out: this piece ensures you don't trip up while stepping into the new season because it works for various climate conditions. Simply pair it with a cropped button-down shirt, trench coat, trousers, and retro sneakers.
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It's guaranteed that you'll likely reach a point at the end of winter when you're really over your sweaters; when that happens, because it will, you'll want to reference this outfit idea again. An easy way to break free from your chunky knits is by swapping them out with a knit shawl—ideally, you'd style the piece over a suit, but it can go over dresses, tanks, and so on.
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Hopefully, you now have a few new sweater styling ideas to get you through the rest of winter. However, should you need a reminder that cold weather won't last forever, imagine the day when you can step out wearing only a turtleneck underneath a shift dress. It's a look that serves as a reminder that our staple sweaters can see us from season to season—if we know how to style them!
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Trust me—this turtleneck will keep you 10 times warmer than you think.
Jasmine Fox-Suliaman is a freelance writer and editor living in New York City. What began as a pastime (blogging on Tumblr) transformed into a lifelong passion for unveiling the connection between fashion and culture on the internet and in real life. Over the last decade, she's melded her extensive edit and social background to various on-staff positions at Who What Wear, MyDomaine, and Byrdie. More recently, she’s become a freelance contributor to other publications including Vogue, Editorialist, and The Cut. Off the clock, you can find her clutching her cell phone as she's constantly scrolling through TikTok and The RealReal, in search of the next cool thing.
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