How and Where to Wear the Best Winter Dresses, According to 13 Vogue Editors
There’s a lot to get dressed up for during the winter holiday season. Thankfully, 11 Vogue editors have perfected at least one fail-safe outfit formula to help get you through the endless list of occasions: winter dresses. Between sweaterdresses ideal for weekend getaways, gala-worthy frocks, and date-night-appropriate black knit dresses, they each bring their own versatility, so long as they’re styled just so.
A satin shirtdress can easily take you from the office straight to a holiday soirée, for example, with a quick swap from an ankle boot to a pair of glitzy heels. A printed cotton dress is as cozy as it is practical: Just add a chunky knit, throw it in your suitcase, and consider your Thanksgiving dinner outfit sorted. An above-the-knee puff-sleeve dress is the perfect pairing with this season’s beloved knee-high boot, according to one Vogue editor who isn’t quite ready to break out her tights. Don’t forget a strapless silhouette either: Layering a turtleneck sweater underneath offers a quick fix for day, while throwing on a blazer transforms it for night. Afraid of the cold? Two editors swear by the dress-over-pants look for the wintry months, whether it’s an effortless, flowy set of trousers or a pair of trusty leggings.
Here, shop the 13 winter dresses Vogue editors are relying on this season, how to wear them, and where to buy them—no matter the occasion.
Kate Spade satin midi shirtdress
$498.00, KATE SPADE
Willow Lindley, accessories director
I have been living in this silky-satin shirtdress from Kate Spade. It is the perfect not-so-basic basic and I love this length with boots.
Bottega Veneta stretch crepe cutout turtleneck dress
$2600.00, SAKS FIFTH AVENUE
Alexandra Gurvitch, market editor
I am obsessed with this keyhole cutout Bottega Veneta dress—it can work for the office, it can work for a date, and it can almost work at temple too.
Marine Moscone striped cotton poplin midi dress
$990.00, MODA OPERANDI
Emily Farra, senior fashion news writer
The perfect shirtdress is so hard to find, but you can’t go wrong with Marina Moscone’s. I love the attention to detail on this one—the band collar, the deep cuffs—and am dying to wear it over pants or leggings this winter. Even better, it’s a dress I can wear all year round; once the weather warms up again, I’ll just swap out my boots for flat sandals.
Khaite Loie ribbed knit midi dress
$1050.00, MODA OPERANDI
Alexandra Michler, director, fashion development
I am very into this Khaite dress. Wear it with a lightweight T-shirt for the office, or with a blazer for cocktails. I love having one reliable staple I can wear all season.
Story MFG Tulsi sheashell print cotton midi dress
$736.00, MATCHES FASHION
Steff Yotka, fashion news editor
I can’t stop thinking about this Story MFG dip-dyed dress with seashell embroidery. It’s happy enough to convince you it’s summer when daylight saving time has you feeling S.A.D.
Tory Burch smocked cotton dress
$498.00, TORY BURCH
Anny Choi, market editor
I love a great shirtdress for fall and winter. This one from Tory Burch is work appropriate, with a touch of romance.
The Vampire's Wife corduroy maxi dress
$1027.00, FARFETCH
Ella Riley-Adams, senior living and beauty editor
I’ve been coveting this corduroy maxi dress from the Vampire’s Wife, which I think would work just as well with Dr. Martens loafers and Kapital socks at the office, as it would with kitten heels for a Christmas party. It’s a rare dress that presents as both elegant and cozy.
Ganni printed mesh dress
$295.00, SHOPBOP
Caroline Griswold, market manager
I love this Ganni dress with its chocolate hues because it pairs perfectly with all the other winter items I’ve been dying to pull out of my closet. I can’t wait to pair it with boots and a chunky knit, or dress it up with some gold jewels. The fabric also makes it super easy to throw in your bag for Thanksgiving without fear of getting wrinkled.
Beaufille Nodus fluted satin midi dress
$940.00, THE OUTNET
Madeline Fass, associate market editor
For someone who’s quite particular when it comes to wearing dresses, there’s no better way to feel the most “me” than by using a dress as a layering piece. The super-low scoop neckline on Beaufille’s Nodus dress is ideal for wearing over both sweaters and turtlenecks, while the uneven midi hem allows me to effortlessly style a pair of trousers underneath and still add the bit of edge I need to feel comfortable. Not to mention, the whole look will keep me warm all season long, which is definitely a plus.
Staud Natasha dress
$295.00, STUD
Lauren Valenti, senior beauty editor
I’ve always found picking a dress for a formal occasion tricky this time of year, but I wore Staud’s Natasha dress to a wedding recently, and it struck all of the right chords. Its halter neckline and structured bodice were sleek and elegant, while its billowy full skirt and side pockets gave it a cozy, sumptuous feel. Not to mention, the color—a rich burgundy is my choice shade as soon as there’s a chill in the air.
Proenza Schouler long wool dress
$790.00, 24S
Julie Tong, commerce editor
I practically live in sweaterdresses during the winter, and this wool knit version by Proenza Schouler is currently my godsend. It fits perfectly over my petite frame without being too tight, nor loose, and hits at that perfect mid-length to show off my boots. It is made of 100% merino wool, which keeps me ultra-warm without being heavy. It’s my go-to dress for the office, weekend getaways, and even date night.
Ganni check print ruched dress
$190.00, FARFETCH
Naomi Elizee, associate market editor
I’m notorious for keeping the summer dream alive, and still rocking my short dresses throughout the fall and winter season. This Ganni dress is the perfect in-between-seasons dress and pairs beautifully with a knee-high boot.
Alexander McQueen tie-neck houndstooth dress
$2375.00, FARFETCH
Lilah Ramzi, features editor
I would very much like to spend the winter in this wallpaper-size houndstooth-patterned dress by Alexander McQueen. It’s mostly wool so it will keep me cozy, plus there’s a scarf built right in. Ms. Burton has thought of everything.
Originally Appeared on Vogue
