How to Dress for Date Night During the Winter

When it comes to dressing up during the winter, all we want to do is hashtag #canyounot and instead dig out roomiest sweatpants, our alma mater sweatshirt, and a nice, thick pair of wool socks. Cozy and cute don’t have to be mutually exclusive though, and since Valentine’s Day is right around the corner, we decided to dig up some style inspiration that’ll keep you snug while you’re out (or staying in) for date night.

Table for Two


If all you’re doing is stepping out of the Uber, into Le Dip, and back again, then there’s no need to freak out about freezing. Brighten up an all-black winter ensemble with a cheerful pink midi skirt, some gold pumps, and a spiky ear cuff just to prove that wearing pink doesn’t mean you’re weak.

Reminisce From Rose embossed midi skirt, $50 at Chicwish; Long sleeve funnel neck body, $38 at Topshop; Pacey pointed high heels, $43 at Asos; Spikes & Studs ear cuff, $24 at Hanuel.

Netflix and Chill


I know, your PJs are tempting if you’re not even leaving the couch for date night, but if you want to up the romance and make it feel more official, you don’t have to sacrifice your comfort. Trade your slippers for loafers, your sweatpants for leather leggings, and your sweatshirt for a silk tunic. Add a statement necklace, and you’re date ready.

Wet-look leggings, $35 at Topshop; Silk Overlook tunic shirt, $98 at Madewell; Mayor pointed flat shoes, $48 at Asos; Margot necklace, $175 at Kendra Scott.

Braving the Elements


Yes, it did just blizzard. Yes, it’s below freezing outside. But what’s more romantic than a stroll down a quiet, snowy street on a winter night? Bundle up for a walk to your restaurant or wine bar in a sweater skirt and chunky knit pullover, and layer with collarless coat in a light color to avoid looking like a dark wool blob.

Gerlanda ribbed sweater skirt, $159.50 at Club Monaco; Barbour Nude Ursula sweater, $199 at Tuckernuck; Steve Madden Wantagh leather ankle boot, $130 at Nordstrom; Contemporary collarless Boucle coat, $45 at Forever 21; Kessler toque, $79 at Kit and Ace.

Associate Editor

Caroline Cunningham joined Washingtonian in 2014 after moving to the DC area from Cincinnati, where she interned and freelanced for Cincinnati Magazine and worked in content marketing. She currently resides in College Park.