How to style a maxi dress for winter, according to stylists

Shirley P. Olin

Winter can put a creative halt on our wardrobe, but there are a few tricks stylists use to don some of our most versatile pieces during cooler stretches. For example, frigid temperatures beckon for more cozy fabrics and loungewear clothes, but you can still look feminine and ultra-chic with the right layering options on a maxi dress.

According to analysis from Trendalytics, there are approximately 120K average weekly searches for maxi dresses. From pleated versions to shirt styles, this garment is a no-brainer to pair with your other seasonal essentials. A maxi is also the perfect transitional piece that offers practicality during a last-minute outfit emergency. With the right accessories and the proper footwear, the maxi dress becomes a foolproof piece to survive winter’s outfit conundrums.

Shop TODAY consulted three stylists for their insight on how to maximize your maxi dress styling and which fabrics will keep you warm yet trendy for the rest of the season.

How to style a maxi dress during winter

The maxi dress can easily be dressed up or casually styled, depending on how your day unfolds. Fashion stylist Melissa Chataigne noted that “a third piece makes an outfit, and by adding a layer to this dress [like a blazer] or even a turtleneck underneath,” it elevates the dress completely. Chataigne also suggested wearing opaque tights and boots for the winter, like the Chelsea style, for the ideal daytime look. “To elevate your outfit for the evening, style it with a fitted blazer or cropped leather jacket and leather heeled boots,” she added.

“The easiest way to wear maxi dresses in the winter is to toss on a long wool or puffy coat for maximum warmth,” personal shopper and stylist Portia LeGall said. For layering purposes, though, she recommends wearing leggings, thermals or thick, insulated tights underneath to keep your legs warm. You can also layer a maxi dress with a cardigan, oversized vest or a chunky sweater “which then turns the dress into a skirt.”

During the night, a maxi dress could be paired with daintier, classier garments for a more elegant vibe. Fashion stylist Andrea Serrano advised on trending fabrics like faux fur, knits, silky satins, fluid velvet, crisp sateen and leather for the winter. “It’s all about playing with proportions so when you layer, keep in mind your body shape. If you are curvy, then wear a blazer, cardigan or slim coat and cinch your waist with a belt. If you have a smaller frame, you can also wear it like that and have options to layer it with a cropped sweater or jacket. [Also], a faux fur stole belted at the waist adds a touch of glam.”

From loose-fitting styles to dresses with pockets, here are some chic maxi dresses to wear during the rest of hibernation season.

Stylish maxi dresses for winter

Red Dress Gray Knit Maxi Dress

This comfy sweater dress will keep you stylish and cozy through the rest of winter. It features side slits to show off your knee-high boots and a turtleneck to keep you warm. It’s the perfect dress you can wear day or night thanks to its versatile color and silhouette.

Zaberry Velvet Cocktail Maxi Dress

Feel elegant on a budget with this velvet maxi dress. All you need is a wool long coat and high heels to add a hint of luxury to the dress. “The material is comfortable and the cut of the dress is very flattering,” added one verified buyer who rated it five stars.

Mango Cut-Out Detail Dress

You can never go wrong with a black maxi dress. This one from Mango offers a modern cut with the cutout detail and A-line silhouette. There are many opportunities to wear this dress day and night. Keep it edgy with leather boots or casual with a pair of sneakers, or wrap around a colorful knit scarf for extra glam.

Exlura Knit Sweater Dress

Look effortlessly chic during winter in this Amazon wrap dress. The soft fabric will complement the rest of your winter clothes, plus this dress is a nice, dressier option for your workweek repertoire. “The best part? This dress is a chameleon. It can be glammed up with heels and a splash of evening jewelry,” noted a verified reviewer.

Anthropologie Slim V-Neck Dress Set

If you’re looking for practicality, this dress set from Anthropologie is the ideal one for lounging and running errands. The set — available in regular, petite and plus sizes — comes with a pullover top and maxi dress to easily mix and match.

Rebdolls Essential Drop Sleeve Bodycon Maxi Dress

This maxi dress features a bodycon fit and an off-the-shoulder neckline for a more elegant vibe. It also comes in different plus sizes and hues that will complement your wintry wardrobe.

Lovestitch River Rock Maxi Dress

Complete your bohemian aesthetic with this maxi dress featuring a side slit. All you need is a pair of insulated tights and booties for a winter take on this piece. The dress also has an abstract motif that pairs well with leather and faux fur elements.

Baltic Born Holly Satin Maxi Dress

Perfect to wear to a winter wedding, this dress is made of soft satin-like fabric and comes with a belt that you can easily adjust to your preference. You should anticipate many compliments coming your way thanks to the flowy material and elegant design.

Lulus Long Sleeve Backless Maxi Dress

With a glowing five-star rating and extensive sizes up to 3X, this gown is the perfect option for your next winter event. Wear it for a wedding, an engagement photo shoot or to your next family party. “This dress fits so beautifully and is beyond easy to wear. The bust is made so that you don’t need a bra, it’ll give you good support,” said one customer.

Asos Satin Maxi Dress

Satin always looks elegant when paired with heels. This maxi dress from Asos features a belt that you can wrap around your waist and a bottom slit for easy movement. No matter the season, this mustard dress offers a transitional color that can be worn day or night and for any occasion.

Zara Knit Dress with Side Buttons

This neutral maxi dress from Zara is ideal for layering pieces over it. You can add a leather jacket and stilettos for a night out, or a pair of kicks with a puffer coat for a comfier feel.

Chico’s Denim Maxi Dress

This easily wearable and flattering maxi dress from Chico’s will become your new go-to weekend outfit. It’s made with chest pockets and a soft denim fabric that offers a relaxed fit. Style it with brown boots for a casual day out, or slip on a pair of heels for an elegant dinner. “It is soft, easy to iron (if you choose) and very comfortable,” added one buyer who rated it five stars.

Farm Rio Hidden Animal Maxi Dress

Add a pop of color to your neutral winter coat with this colorful dress from Farm Rio. The intricate and tropical-inspired motif will transport you to an island even during frosty days. Layer a chunky turtleneck underneath when you need extra warmth.

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