21 Winter Date Outfit Ideas That Are Cute and Comfortable

Date night during the winter months can be a tricky event to navigate. Something you typically look forward to can become something you dread. Trying to put together an outfit that won’t leave you feeling cold or uncomfortable but still make you feel like the best version of yourself is a particularly difficult task. Throw a pandemic into the mix, and well, winter date nights really can’t be totally spontaneous. The little dress or pretty top you reach for during the warmer months just won’t cut it in the wind, rain, or snow. 

We’re here to help with a slew of outfit ideas that will turn winter date nights into the fun, romantic activities that they’re meant to be, even in cold weather. Just because it’s cold outside doesn’t mean you need to sacrifice your style or relationship building. From leather pants to sweaterdresses to belted trench coats, we’ve got your outfit covered to ensure you feel cute while remaining comfortable. Whether you’re dressing up to safely dine outside or stay in, below are 21 winter date-night outfits that you’ll actually want to wear. 

On Lydia Tsegay: H&M pants; Zara bag. Leather pants always lend a cool vibe, and a fitted sweater balances out proportions. 

On Débora Rosa: By Malene Birger set. A knit set always looks elevated. 

On Franny Fyne: Who What Wear Collection bag. This feminine sweater and skirt juxtaposed with edgy combat boots create a perfect balance. 

On Nitsan Raiter: Prada bag; Charlotte Simone coat; I.Am.Gia pants. A furry coat feels especially fun when paired with patent-leather pants and boots. 

A matching sweater and knit skirt are equal parts cozy and chic. 

On Tania Sarin: Carolina Herrera dress. It doesn’t get any cooler than a printed maxi dress and knee-high boots. 

On Lee Litumbe: Fendi coat; Dior belt. A belted coat is as timeless as it gets. Throw one on over an all-black outfit for instant polish.

On Monikh Dale: Christoper Esber Convertible Ribbed Dress ($880). A ribbed-knit dress with cutout detail is guaranteed to garner compliments. 

On Jen Ceballos: Prada boots; Nisse Eiko Leather Trench Dress ($380). A leather dress is cool on its own, and adding knee-high boots just doubles down on that fact. 

On Lisa DiCicco Cahue: Helmut Lang Cutout Turtleneck ($175); ReDone ’70s High-Rise Jeans ($275). A cutout sweater adds interest to any outfit. 

On Shalini Acharya: & Other Stories sweater; Celine sunglasses; Vince dress; Bottega Veneta Mini Jodie Bag ($1720); Gucci loafers. A cardigan and slip dress are a classic date-night combination. Just throw a coat over it and you’re ready for winter. 

On Jill Wallace: LNA Martin T-Shirt ($90). A belted blazer dress can go from fall to winter with the simple addition of tights.

On Sabina Socol: Miista boots. Never underestimate the power of a cozy sweater, perfectly fitting jeans, and luxe-looking boots. 

On Nnenna Echem: Bik Bok top. Here’s proof you can never go wrong with a hint of sparkle and a red lip.

On Lauren Johnson: Orseund Iris Night-Out Open Back Blouse ($540). An open-back top is always a good idea for date night, and leather pants make it feel seasonal.

On Eni Ilori: AllSaints dress. Throw your favorite slip dress over a long-sleeve top of similar color for a sophisticated, monochrome look.

Top off the classic combo of a blazer dress and over-the-knee boots with fun glitter earrings. 

A turtleneck-blazer combination is a classic, so pairing the pieces with leather pants and boots keeps the look feeling special. 

On Emili Sindlev: A.W.A.K.E. Mode Vegan Leather Skirt ($680). Although you may need to add a coat, the pairing of a sweater and leather skirt is one perfect outfit. 

On Ellie: The Frankie Shop Pernille Oversize Blazer ($240). Not only is a tailored suit classic, but it’s also ultra-comfortable. Just add heels to make it feel date night–ready.

On Yamila Orozco: Violeta by Mango blazer. Make your leather shorts work for winter by layering them over sheer tights for a night out. 

Look at this color.

Just the right amount of skin.

For those chilly winter nights.

If you prefer your cutouts with a twist.

Pair this with a slip skirt and stilettos.

Be the center of attention.

Make an impression.

This would look amazing with knee-length boots.

Next, 29 Elevated (Yet Affordable) Tops That’ll Make Your Skinny Jeans Look So Good

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