A dark purple turtleneck, black slip dress, silver heels, and black headband with pearl detail.

The Best Winter Date Night Looks Are Both Sexy and Cozy

Date nights—and, quite frankly, nights out in general—during the winter pose a frustrating conundrum. What do you wear that’s both sexy and warm enough to keep you from freezing the entire time? Finding the perfect combination is tricky—but it’s not impossible. (!) Pairing classically cozy pieces with undeniably sleek and sultry clothing is a simple and effective way to create that balance in plus-size winter date outfits. So go ahead and make those plans with your boo, bb. You’re about to look fierce as hell.

To create the ideal winter date night outfit, all you need is a little bit of creativity—and this guide, of course. These outfit recipes aren’t necessarily complicated, but they do require a bit of forward-thinking. Before you plan your ensemble for the evening, make sure you consider your own body temperature (no matter how freezing it may be outside). If you always get warm inside restaurants, maybe try a look with layers you can shed just in case. Or, if you’re constantly cold even when the heat is on full blast, choose thicker fabrics—and remember to bring a coat, too.

Taking into consideration how warm or cool you might get when you’re not outdoors is (almost) as important as the outfits themselves. So once you factor that in, it’s time to start prepping that lewk. From the underrated turtleneck and slip dress combination to ways to make an oversized blouse and leggings look sexy AF, these plus-size winter date outfits are here to make sure you look incredible and stay nice and cozy.

P.S. All the shoes featured below are available in wide widths. You’re welcome.

Here at Unruly, we’re committed to featuring plus-size pieces we genuinely love and want to share with you. We’re connected to an affiliate revenue program, which means we might make a small commission when you buy products through our shopping guides. This in no way affects the pieces we choose to feature, and it never will. (Confused? We’d love to answer any questions you have about this. Email us at beunrulyinfo@gmail.com!)

1. The Slip Dress & Turtleneck Combo

One of the sleekest and coziest ensembles for winter is the combination of a turtleneck and slip dress. The vibes are sexy, but you won’t freeze your buns off when the temperatures are low. Keep the hues dark and mysterious, then add a few metallic accessories to liven things up a bit.

A dark purple turtleneck, black slip dress, silver heels, and silver purse.

shop the look

top — $33.30 from Torrid
dress — $20 from Nasty Gal
shoes — $169 from Good American
bag — $59.39 from Topshop

2. The Oversized Blouse & Leggings Made Sexy

There’s nothing quite as comfortable as leggings and an oversized top—and now you can make that look ideal for date night, too. Try a pair of faux suede leggings paired with an oversized satin blouse for a look that’s equal parts comfy and sexy. Then, add some fun booties to top it all off. Voila!

A satin shirt, brown faux suede leggings, green booties.

shop the look

top — $17.99 from H&M
leggings — $23.70 from Torrid
shoes — $64.60 from ASOS

3. The Sequin Pants Are Everything ‘Fit

Winter is the perfect time to wear sequins—so do yourself a favor and make ’em work for date night. Throw on some black sequin pants with a cozy pullover sweater, trendy headband (Blair Waldorf style), and heels. You’ll feel totally festive, but comfort and warmth aren’t sacrificed in the least.

Black sequin pants, red sweater, black headband with pearl detail, and black heels.

shop the look

top — $98 from Madewell
pants — $34.99 from H&M
shoes — $65 from Topshop
headband — $54 from Zaxie

4. The Sweater Dress & Thigh-High Boots Look

A sweater dress might be the easiest way to get dressed up in the winter, folks. And to make the look totally date night appropriate, add some thigh-high boots and sparkly, elegant earrings. Before you know it, all eyes will be on you.

A striped sweater dress in black, purple, and blue, thigh-high black boots, and silver earrings.

shop the look

dress — $47.70 from Torrid
shoes — $345 from Good American
earrings — $36 from Zaxie

5. The Always-Chic Leopard Skirt Ensemble

The leopard skirt will never get old—and it makes an incredible base for plus-size winter date outfits. Add a simple black mockneck or turtleneck, black blazer, and some fun neutral heels. This is one outfit recipe that will never go out of style.

A sleeveless black turtleneck, leopard print skirt, black blazer, and tan heels.

shop the look

top — $13.50 from Torrid
skirt — $29.99 from H&M
blazer — $158 from Madewell
shoes — $189 from Good American