38 Winter Date Outfits That'll Keep You Warm While You Try to Play It Cool
Cozy and cute is our favorite combo.
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No matter the time of year, one thing is for sure—dates will always go on! But I can totally get why winter dates might feel especially challenging. Putting together winter work outfits is already a huge challenge (thanks to freezing temps, snow, and ice!)—but dressing for a date during the coldest season of the year is on an entirely different level. After all, your goal is to dress in something that makes you feel confident and warm. But in the dead of winter, it's difficult to find motivation to do anything other than bundle up in your sweats and watch a ton of rom-coms (just me, or...?). But don't worry—nailing down the perfect look doesn't have to be complicated. There are plenty of stunning winter outfits that combine style and warmth, and I'm here to help you find them.
Need some winter fashion inspo? What you wear really comes down to one crucial detail—the occasion! A cozy dinner and drinks calls for something totally different than an afternoon of ice skating and sipping hot chocolate. But no matter what the plans, we've got you covered with options for every scenario. Yes, even for those times you're a plus-one at a winter wedding or get that last-minute dinner party invite. From casual brunch-ready looks to elevated evening ensembles that'll make you feel amazing, we've compiled 38 different winter outfits for any get-together. The best part? Now that your outfit is sorted, you can focus on what really matters—like deciding whether to share that molten chocolate dessert!
There's practically nothing worse than being cold so why even risk it at the game? You'll be the coziest person even at halftime in this puffer jacket that belts in at the waist to keep you lookin' cute. Style it with some thermal leggings or jeans and all-black accessories for a chic gameday-ready look.
Out for a winter walk? This comfortable boyfriend hoodie and fleece sweatpants create the perfect laid-back look. Layer a long wool coat over top to add sophistication and extra warmth—it's the ideal blend of cozy and polished for a casual afternoon outdoors.
Take in beautiful art with a jumpsuit, a statement bag, and sleek black booties.
This halter top and ruched maxi skirt combo is guaranteed to make you feel confident and comfortable. Layer it with a cropped jacket or wrap to stay cozy during your evening out—the maxi length adds extra warmth while keeping the look elegant for dinner and drinks.
Trust me, you'll be glad you wore an easy sweater dress to go browse some shops, especially if you decide to try things on while you're out. Add in some tall boots to keep you toasty throughout the day.
This halter top and ruched maxi skirt combo is guaranteed to make you feel confident and comfortable. Layer it with some fleece-lined tights and a long coat to stay cozy during your evening out—the maxi length adds extra warmth while keeping the look elegant for dinner and drinks.
If sailing with your dreamboat is on the agenda, this sweater strikes the perfect balance—it offers a subtle nod to nautical style without going full sailor. The modern take on the classic Breton stripe keeps things sophisticated yet playful, perfect for sipping champagne on deck or watching the sunset from the bow. Layer it over a thin thermal base and add a cozy scarf to stay warm against those chilly ocean breezes.
After you hit the slopes you'll want to cozy up in a cute coat while you sip your mulled wine- this coat will make you look like you already have a season pass even if you don't even own skis.
Need a solution for those last-minute invites that send you into a wardrobe panic? Let me introduce you to your new go-to: this versatile maxi dress. This super comfy maxi dress will match any shoe you own and will help you look polished yet playful in a pinch.
We get it, you've been wearing your go-to sequin dress on repeat for concerts but you're kinda over it. This flared pant feels just as special but you'll actually be able to dance in these. Plus, you can wear pretty much anything up top since metallics work as a neutral.
Stay warm and cute at the rink in this plush statement coat. Add matching earmuffs for extra coziness—whether you're gliding on the ice or holding onto the rail (no judgment here).
The girlier the better when it comes to girls' night out, amirite? This red and pink number would look even cuter with a sparkly bag or clutch. Don't be afraid to double up on pink or red, either!
Meet your new secret weapon for maximum comfort without sacrificing style: these ingeniously designed sweatpants that perfectly mimic denim. The cotton fabric features a convincing jean print, giving you the polished look of your favorite denim while feeling as cozy as your most comfortable sweats. It's the best of both worlds for those days when you want to look put together with minimal effort.
A halter dress with a slit feels like the perfect dress to wear to a candlelit dinner. Pair it with some statement earrings for a romantic date night look.
Long travel with your honey call for foolproof dressing. This matching knit set is equal parts cute and polished so even if you didn't get any sleep on the train ride over, you won't look like it.
Going to a sports bar in a teeny dress isn't always the move. If you want to feel a little more casual but still feel date-night ready this top pairs beautifully with everything from jeans to a leather skirt.
Never leave your house in coat you're afraid to get poured on again. Everyone should own a trench, plus it's the perfect topper to jeans and a tee during transitional weather.
Meeting friends should feel more casual, you never want to look like you tried hard (even if you did). A denim jumpsuit feels so chic and cool girl while still looking relaxed. Pair a shearling jacket on top for a retro-inspired ensemble.
We're guilty of sneaking in a blanket to the movies, but now we don't need to. This cashmere cape essentially takes the place of a cozy throw. It looks cute draped over light-wash jeans and chelsea boots in case you decide to go out for drinks after the movie.
Turn heads all night long in this scarlett stunner. Black tie just means the fanciest of the fancy and this dress gives fancy and glam in the best possible way. Rock this gown with your sky high pumps and clutch for the most gorgeous and memorable 'fit.
Tarah-Lynn Saint-Elien is the fashion editor at Cosmopolitan, writing weighty and witty stories that run the gamut of gushing over Zendaya to convincing you of everything you need in your closet! She began her journey in the industry with a fashion and faith blog and an internship at Elle about 10 years ago. Since then, she's also served as the style editor at The Haitian Times. The Haitian-American pageant queen is Miss Supranational Haiti 2024, a Syracuse Masters graduate, and the author of three books, including: Claim Your Crown. Follow her on Instagram and TikTok: @iamtarahlynn.
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![london, england june 16: elizabeth hurley and billy ray cyrus attend the royal academy of dance fundraising evening at mandarin oriental hotel on june 16, 2025 in london, england. (photo by jeff spicer/getty images)](https://hips.hearstapps.com/hmg-prod/images/gettyimages-2220449960-685177c1f3a0c.jpg?crop=1.00xw:0.668xh;0,0.0662xh&resize=360:* ""Royal Academy Of Dance Fundraising Evening" - Arrivals")
