54 Winter Maxidresses to Live in All Season Long

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Cold weather can really put a damper on your style. Unless, of course, you’ve prepped your wardrobe with seasonally fit staples. It doesn’t get cozier than the best winter maxidresses when you’re in the mood for a throw-on-and-go piece. Yes, indeed, coats, essential sweaters, boots, and chill-proof accessories are critical for a stylish bundle. But for total ease, ankle-grazing maxis—from sweaterdresses to versatile black and winter white designs—equate to cozy-chic comfort in an instant. Similarly, luxe leather, suede, and cashmere styles epitomize the winter season with polished panache. At the same time, velvet, silk, and beautiful prints are well suited to dressier moments.

When you think about it, there’s almost no occasion when a winter maxi won’t work. They appear effortlessly polished at work, unassumingly alluring on a date, and festive for parties, from holiday gatherings to weddings. And even better, the effort always feels minimal when dressing in your favorite style, requiring just a few accessories to complete the look. Like a pair of boots, be it a block-heeled silhouette or sumptuous suede style, or heels, such as pumps, kitten heels, or party sandals befitting occasions. A top layer is essential when braving the elements in a winter maxidress too. A fleece denim jacket or puffer will lend extra warmth on casual days, while timeless wool and jacquard designs are elegant when dressing up. Finally, of course, you won’t want to forget jewelry—perhaps a zodiac pendant or earrings for a personal touch? Or a sculptural piece of silver mixed with a few delicately layered gold pieces. Keep scrolling to discover Vogue’s edit of the chicest winter maxidresses, from casually elegant to sophisticated to charmingly festive.

The Knitted Dress

The ultimate winter maxidress is unquestionably a knitted style, whether your silhouette of choice is fitted, A-line, or straight, detailed with a self-tie belt.

Emporio Armani stripe long-sleeve maxi dress

Banana Republic Johnny-collar sweater dress

Totême ribbed wool maxi dress

Chloé cashmere and wool-blend maxi dress

The Leather and Suede Dress

For statement-making moments, a winter maxidress cut from leather or suede is the epitome of bold, whether for an important meeting, special dinner, or cocktail soiree.

Jonathan Simkhai Kelli faux-suede shirtdress

Gabriela Hearst Julian whipstiched leather maxi dress

Joseph Casia suede and leather maxi dress

Aliétte belted patent leather maxi dress

Proenza Schouler pintuck long-sleeve lamb-skin leather dress

Isabel Marant Genazuli faux-leather maxi dress

The High-Neckline Dress

Mock and turtleneck dresses are staples in the cold; when going the maxi route this season, dresses vary from subtly sophisticated to casual and vibrant with cutouts.

Proenza Schouler wool knit twisted maxi dress

Bottega Veneta turtleneck jersey maxi dress

Philosophy di Lorenzo Serafini striped turtleneck pleated maxi dress

Mango knitted Perkins neck dress

Rebecca Taylor flounce-sleeve cotton blend maxi dress

Christopher Kane cutout wool-cashmere maxi dress

The Cashmere Dress

Few things are as luxurious as cashmere. So why not envelop yourself in a winter maxidress knitted from the sumptuous fabric?

Petar Petrov Aza roll-neck cashmere-blend dress

$2,060$1,648

MATCHESFASHION.COM

Extreme Cashmere N°106 Weird cashmere-blend maxi dress

Michael Kors Collection cashmere turtleneck dress

Polo Ralph Lauren off-shoulder cashmere maxi dress

Johnstons of Elgin roll-neck ribbed-cashmere maxi dress

$679$543

MATCHESFASHION.COM

Lauren Manoogian cashmere-blend turtleneck maxi dress

The Winter White Dress

For a masterful take on winter white, it doesn’t get more effortless than a 
maxidress—shades of cream definitely count.

Lisa Yang Lauren ribbed-cashmere maxi dress

Co Natural World wool maxi dress

Ronny Kobo Eire cable-knit open-back maxi sweater dress

Gauge81 Rubi rib-knit dress

Atu Body Couture open-back long-sleeve maxi dress

Auteur Clara pleated knit maxi dress

The Velvet Dress

You’ll make an impact on the holiday-party circuit in a velvet maxidress, be it a turtleneck, ruffled, or elegantly spliced design. You can even wear one for work with a smart blazer in the mix.

L’Agence Cameron velvet maxi shirt dress

ALC Katherine cutout velvet maxi shirt dress

Lela Rose Devore plaid velvet maxi dress

Saloni Camille crystal-bow velvet midi-dress

Pat Bo Strass velvet long sleeve maxi dress

Batsheva Carol ruffled crushed-velvet maxi dress

The Black Dress

There’s no shame in defaulting to black, especially when it’s a beautiful 
maxidress for understated chic.

Jacquemus Obiou cutout woven maxi shirt dress

Brandon Maxwell removable micro cardigan maxi dress

Zara knit dress with zipper

Raey hooded knitted cashmere maxi dress

Norma Kamali long-sleeve turtleneck dress

Victoria Beckham pleated maxi dress

The Printed Dress

Whether for a party or a sophisticated daytime look, you’ll make a splash in a printed winter maxidress with long sleeves.

Tory Burch printed sheath dress

La DoubleJ long-sleeve swing dress

Doên Eugenie lace-trimmed floral-print crepe dress

ByTiMo floral crepe maxi dress

Johanna Ortiz Illuminating Glimpse tie-detailed floral-print satin-jacquard maxi dress

The Silk Dress

The ultimate day-to-night winter maxidress is, indeed, one crafted from silk. Naturally some skew more formal than others—in that case, reserve it for an elegant party.

Roland Mouret Ivel silk georgette maxi dress

Altuzarra Lucie dip-dye silk shirtdress

Christopher Esber Triquetra cutout silk-satin maxi dress

J.Crew Collection tiered silk-chiffon tuxedo dress

Khaite Carlo gathered silk maxi dress

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