Do you feel the cold front coming on? Like it or not, winter is coming. While some may relish the idea of colder temperatures, I can’t relate. Don’t get me wrong. Some things about this season are wonderful—the start of the gifting season, the prospect of new trends, and even all the chic coat options. But just because winter is coming doesn’t mean I’m ready to part ways with my dresses. As much as I know I “should” want to slip into a pair of trendy jeans or leggings, I just don’t have the desire to deal with them. I find the whole process of putting on pants daunting, so I try to circumvent it as much as possible. You could say I’m in denial, especially considering the cold temperatures, but I know I’m not the only one who feels this way. If you clicked on this article, you, too, aren’t looking forward to the potential prospect of packing away your favorite frocks. Frankly, I don’t blame you. There’s an ease that comes with just throwing on a dress and heading out the door, and it’s hard to part ways with them, even if the weather tells us otherwise. It’s why I’ve spent so many years dedicated to figuring out how to wear dresses in the winter without sacrificing warmth. One way to pull off this seeming “impractical” look is by choosing the right types of dresses (e.g., leather or sweaterdress options) and being intentional with styling. Knowing how to layer correctly is half the battle of making any dress winter ready—it’s an art form. While it takes a great deal of expertise to make dresses work in the winter, you can learn it. In an effort to share some of my knowledge, I’ve done hours of research to create a comprehensive blueprint on how to wear a dress in the winter. Ahead, you’ll find 24 winter dress outfit ideas, styling tips, and shopping recommendations to make you less weary about wearing them in the winter. Consider this your permission slip to skip out on pants this winter.
The secret to pulling off dresses in the winter comes down to having one staple on hand: a sweaterdress. When in doubt, you can’t go wrong with pairing a longline coat with a maxi sweaterdress and ballet flats—it’s a failproof formula for easy and elegant winter dressing.
Normally, coats this long cost double the price.
Insider tip: Zara has some of the best sweaterdresses on the down-low.
While it’s definitely better to opt for dresses made from thicker textiles in the winter, that doesn’t mean you must. In fact, you can make the more summer-feeling white maxi dress work for winter by layering a crew-neck sweater over it and adding colorful socks or hosiery.
Crew-neck sweaters never cease to be chic.
Aren’t these little red socks so precious?
Just because it’s cold outside doesn’t mean you can’t look cool. (Excuse the pun.) When it comes to dressing for winter, don’t be afraid to ditch your pants in lieu of wearing a black ribbed dress with a moto jacket, pumps, and a crescent shoulder bag. It’s a look that will work for whatever winter plans are on your agenda.
The worn-in distressing on this jacket makes it look designer.
You’ll want to carry this all winter long.
Do you consider yourself more of a minimalist? Rather than committing to a moto jacket, make a minor swap to a timeless leather trench. Styling this outerwear over a turtleneck sweaterdress with simple accessories will embody the ’90s-minimalism aesthetic.
One of the hardest things about dressing during the winter is being able to choose what to wear for various occasions, including work. If you’re like me and don’t want to part with your dresses, then there’s only one thing you can do: invest in a leather dress. Not only will opting for this textile ensure you stay warm, but it’s also the perfect staple for the office. Make it feel formal by pairing it with a knitted polo, pumps, hosiery, and outerwear.
Chic, chic, chic.
You’ll wear these well into the spring.
It’s not just dressing for work that’s a challenge. If I’m being honest, no one wants to wear a million bulky layers on a date—hence the appeal of dresses. If you’re worried this item won’t work for your winter-date plans, take inspiration from the look above. Opt for a fitted knit dress with tights, pumps, sculptural earrings, a clutch bag, and a coat with a built-in scarf.
Our entire editorial team wears these earrings on repeat.
Nothing is more flattering than a sweetheart neckline.
Another way to ensure your dresses are equipped for cold weather? Always opt for base layers, like the look above. Even if you’re planning on wearing thermal tights or a thick winter coat, it’s worth layering a light turtleneck underneath a minidress to ensure maximum warmth.
Pro tip: Look for a thinner turtleneck when you’re planning on layering the item underneath your dress to ensure it can be a proper base garment that’s not too bulky.
These boots are made for walkin’.
Not only can minidresses be made winter ready by layering, but so can sheer ones! Don’t believe me? Look at the outfit above. By layering your sheer dress over trousers and underneath a chunky turtleneck, you can extend the item’s life cycle and add visual intrigue to any otherwise simple winter outfit.
You’ll never regret investing in a great turtleneck.
Make these Mary Janes more winter ready by pairing them with tights or socks.
At the risk of sounding like a broken record, I’m going to reiterate that the key to wearing dresses in cold weather is through layering. Yes, it helps to put on a chunky leather bomber jacket over a knitted dress, but the most important element is adding thermal underpinnings. Whether you choose to layer exposed leggings or add a pair of hidden tights underneath your dress, you will not regret adding the extra layer.
Cool girls, apply here.
Not to be dramatic, but it will change your life if you start layering thermal leggings underneath your dresses in the winter.
Ample layers are required to make dresses more winter-proof for those in cold climates. If you are lucky enough to live somewhere warmer, you may not need to add thermal underpinnings or oversize overcoats into the mix. If that’s the case, style a well-tailored wool blazer over a dramatic dress with pumps or boots to make your frock feel wintry.
The nipped-in waist on this blazer is sublime.
Now, here’s a dress that’s so pretty it can’t possibly be put away during the winter.
If a blazer won’t cut it, you’ll want to turn to a cozier option like a puffer coat. While this outerwear might not seem like the most flattering silhouette, it can be if styled right. Take a cue from the outfit above and pair the coat with a sweaterdress, a headband, a woven shoulder bag, thermal tights, and ballet flats.
Aritzia’s puffer jackets are worth every penny.
Consider these a long-term investment.
Not a fan of puffer coats? I totally get it. You can still be warm without feeling like a toasted marshmallow by opting for a wrap coat. Style the outerwear over a thick turtleneck sweaterdress with tights, socks, and knee-high boots for a cozy yet chic winter ensemble.
Scarf-coats are the item of the season.
The perfect boots for schlepping through the snow.
In addition to the wrap and puffer jacket, a tailored double-breasted coat works well for making your dresses winter ready. Just be sure to draw inspiration from the outfit above and add trendy elements into your look—like a headband, sunglasses, tights, and Mary Jane shoes—to ensure the outfit works.
Gasp! Gosh, this is a good coat.
Calzedonia’s thermal tights will make all your dresses winter-proof.
Consider this your sign that a coat is not the only way to winterize your dresses. By styling a turtleneck dress underneath a chunky zip-up jumper with knee-high boots and a shoulder bag, you get the same functionality as other winter outfits with half the bulky layers.
The merino fabrication ensures that this knit will be extra warm.
Everyone will think this simple flap bag is designer.
In addition to adding a jumper to the mix, you can opt for other knitwear—ahem, sweater-vests. Take this preppy staple and give it the cool factor by pairing it with a puff-sleeve dress, combat boots, and a furry handbag.
Massimo Dutti rarely disappoints.
Almost every New Yorker lives in these boots during the winter.
For those who love the idea of layered knitwear but know a sweater-vest won’t be warm enough, you’ll want to take a cue from the outfit above. When you style a duster cardigan over another knit dress with knee-high boots, you’re sure to be warm. If you’re worried about layered knits looking too bulky, add a belt for final measure.
Zara does it again.
Styling tip: Make all of your bulkier winter knits more formfitting by adding a belt.
Stacking on the knits is a safe bet to ensure your dresses are fit for cold weather. But if you want to be a bit more daring this winter, then consider re-creating the look above. Styling a knit dress over denim with interesting accessories is a surefire way to spice up your staple sweaterdress.
Santa, if you’re reading this, you know what to do.
In the winter, try opting for baggier or wide-leg denim silhouttes that allow you to layer thermal items underneath for extra warmth.
On top of jeans being a great way to winterize dresses for the winter, so are leather trousers. These bottoms can make oversize sweaters that tetter into tunic territory less intimidating to wear. For an effortlessly elegant winter ensemble, pair a tunic sweater with leather trousers, a sleek shoulder bag, and either mules or boots depending on the weather.
So cozy.
Leather pants are a must-have for any winter wardrobe.
Possibly one of the easiest ways to make any dress warmer (besides pairing it with denim or leather) is to reach for a shearling jacket. Throw this fuzzy coat over a knitted dress, and it won’t matter what the temperature is outside because you’ll be toasty.
You may not own a ski chalet, but this coat will make you feel like you do.
Look for knitted dresses with wool or merino blends to ensure they’re as warm as possible.
Yes, I’ve already mentioned how fuzzy coats can make dresses feel 10 times warmer, but did I mention they can make them look cooler too? Even the simplest black knit dress can stun with the addition of a statement fur coat, a scarf, chunky lug-sole boots, and a shoulder bag.
Made from faux shearling and leather, this coat is sure to keep you warm.
Nordstrom’s sweaterdresses are a must-shop for the winter.
While donning a statement coat is undoubtedly an easy way to make any dress stand out in the drab winter months, it’s not the only way. For the minimalists reading this story, one simply needs to play with contrasting neutrals to attract the same amount of attention. Draw inspiration from the look above by taking a gray coat and silver accessories and styling them with head-to-toe black for a look that’s just as visually intriguing.
Little black dress, but in knit form.
Just imagine how chic this bangle would look layered over a pair of leather gloves.
When you really want your new knitted dress to be the center of attention, you’ll want to ensure your styling honors that desire. What better way to do just that than by adding leather opera gloves? Not only will this accessory keep your hands warm, but it will also draw attention to your dress. Note: Should you need a few extra layers, you can always add thermal undergarments and/or a minimal coat.
You can also shop these gloves in white and brown.
Scandi brands have the best knitwear.
Besides the notion that you “must” pack away your dresses, one of the worst things about winter is the sensation of having cold feet. Luckily, there’s a solution to both quandaries: the outfit idea above. Styling a maxi dress with a longline trench coat and fuzzy shoes allows you to walk the fine line between opting for functional winter items and having fun with fashion.
It’s a need, not a want.
Buh-bye, cold feet!
By now, you hopefully have plenty of ideas on how to wear a dress in the winter. But if you’re in need of one last nugget of wisdom, let it be this. It’s all about styling. You do not have to follow “rules” about what you should be wearing in the winter, nor do you have to pack away your dresses. You just need to be willing to make a few simple swaps to make your dresses winter-forward. For example, a simple ribbed dress doesn’t need to be styled with sandals. Rather, you can pair it with ankle boots and a longline coat. At the end of the day, any dress can be a winter dress if you dare to make it one.
Sublime. No notes.
The slit on this dress will allow you to show off your favorite boots.
