How to Wear Dresses in the Winter Without Sacrificing Warmth

With the proper layering tactics, of course.

dresses in winter

Extreme temperatures have a knack for relegating many of us to style uniforms. In order to brave New York City’s coldest days, I often forgo capital “F” fashion and gravitate toward the chunkiest knitwear I can find. That said, it is possible to circulate the more fanciful items in your wardrobe and still maintain warmth—if worn correctly. This week, we’re talking about dresses, honing in on the way stylish women don the feminine staple in the winter. The results all stem from the same foundation: layers. Whether they are in the form of slouchy knitwear or slinky turtlenecks, here are three outfit equations to keep your dresses in rotation all winter long.

Crochet Maxi + Slouchy Cardigan + Socks

style equations

Right photo: Courtesy of Instagram/@barbarasantiago.r

When in doubt, pile on the knits. Bárbara Santiago shows us that crochet can, in fact, be worn throughout the colder months, if styled correctly. She’s opted for a neutral cardigan, lug-sole loafers, and a pop of color in the form of cherry red socks.

Ace Knit Cardigan

Birgitte Herskind

Paloma Beanie

Cinq à Sept


Rowing Blazers
$15 $12

Floral Midi + Leather Trench + Turtleneck

style equations

Right photo: Courtesy of Instagram/@simimoonlight

Breath new life into that summery floral dress by mixing it with a leather trench and heavier booties. A bright turtleneck serves as the meeting point between these seasonally polarized essentials.

Wrap Maxi Dress

Farm Rio

Shopping Bag


Prairie Dress + Sweater Vest + Tights

style equations

Right photo: Courtesy of Instagram/@mafaldapatricio

To carry your favorite prairie dress into the colder months, add a sweater vest or knit bib—the perfect complement to the overall kitschy feel. Tights and all-weather boots keep this particular look rooted firmly in practicality.

Cable-knit High-neck Bib

Jil Sander
$650 $390

Raining or Not

H20 Fagerholt
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