Crafting a can't-miss ensemble in the winter can be a huge challenge (thanks, freezing temps!)—but dressing for a date during the coldest season of the year is on an entirely different level. After all, your goal is to look cute AND stay warm. Unfortunately, those don't always go hand in hand, and 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 if you do happen to swipe right on a special someone—or have an upcoming date with your S.O.—and want to dress to impress, there are plenty of stunning winter date outfits to try.
Like dating during any season, your ensemble will vary depending on the activity. What you'd wear to dinner and drinks is definitely different than your look for an ice-skating date. No matter what the plans, though, we've got you covered. From casual, low-key vibes to bougie lewks that'll knock your date's socks off, we've compiled 21 different winter outfits for any get-together. And since your 'fit is officially sorted, you can shift your focus to those romantic sparks. Just don't do anything we wouldn't do!
1
For a Candlelit Dinner
Shimmer Wrap Dress
If it's a fancier occasion like dinner and drinks, a shimmery wrap dress will make you feel confident for the night ahead. Throw on a stylish faux-fur coat and lucite heels to dress it up even further.
2
For a Neighborhood Jaunt
Lanigan Turtleneck
Taking a romantic stroll around the neighborhood without totally freezing? It's possible! Just bundle up in a classic knit turtleneck, faux leather pants, and your warmest (and cutest) coat.
3
For a Movie
Nomi Cutout Sweater
Sometimes watching a flick is a great way to connect, especially if you two are movie buffs. Keep it simple but still fashionable in a cutout sweater, wide-leg jeans, and booties. Then, after the film, you can put on your puffer coat to head outside and discuss your hot takes.
4
For a Post-Work Date
Maxi Sweater Skirt With Slit
A moto jacket and sweater skirt is perfect for a dinner date after office hours. You won't seem overdressed, and there's no need to worry about bringing extra clothes to work.
5
For a Barcade
Warped Checkered Print Super Soft Flare Pants
Arcades aren't just for kids, ya know. Go to a local one and grab a beer in a cozy sweater and fun printed flares for a game night filled with Pac-Man and Donkey Kong.
6
For a Cocktail Date
Simone Satin Wrap Shirt Dress
Just because it's cold outside doesn't mean you have to put away all your LBDs, so get ready for a night out with this satin wrap dress. If you're meeting up for cocktails at an upscale bar, a martini glass makes a great accessory to this number.
7
For a Low-Key Date
High-Rise Roadtripper Authentic Skinny Jeans
Frankly, you can't go wrong with a classic mockneck sweater, jeans, and mules for a casual date. It's a combo that'll stand the test of time—and it looks really, really cute.
8
For a Farmers Market Trip
Oversized Knitted Midi Dress
A maxi sweater dress looks surprisingly effortless, which is great for a low-stakes date like walking around a farmers market. If you end up hitting it off, you can grab some food and take the conversation to a second location.
9
For a Day Trip
Midi Smock Dress
The best part about long dresses is that they can be a part of your wardrobe all year round. Pair this polka dot one with a black coat and chunky boots, and you'll be comfortable but cute for any travel plans.
10
For a Glass of Wine
Dasha Midi Skirt
A fun skirt is always a good move, and you can throw on a pair of tights for more warmth if needed. Coordinate with a slouchy white sweater and white zip-up boots for a cool winter 'fit.
11
For a Bookstore Date
Cashmere Sleeveless Turtleneck Tunic
Through your online chats you both figured out that you love a good read, so a cozy bookstore with a cafe inside and some nooks for chatting is the perf location. A sweater vest tunic tossed over a shirt dress is a great 'fit to impress your date.
12
For Looking at Lights
Long-Sleeve Rib-Knit Striped Midi Sweater Dress
PSA: You don't have to put your dresses away when it's cold. A knit turtleneck one keeps the cozy vibes going when the temps drop, and it looks great with your fave everyday booties. The low heels will save your feet when you're walking around and chatting for hours on end.
13
For a Concert Date
Majori Blouse
The beauty of the faux leather pant and blouse combo is that it's so incredibly simple—but, of course, looks so chic. Add a necklace and some funky boots if you're headed to a concert.
14
For a Fancy Date
Felicity Dress
A velvety slip dress takes a classic silhouette and brings it up a notch. Pop on some statement earrings and your cutest heels to complete this gorge ensemble.
15
For Ice Skating
Water-Resistant Metallic Puffer Jacket
Want to wear something more unique? Opt for a colorful puffer to really make an impression on (and off!) the ice. Wear a fun floral blouse underneath and put on a pair of flare jeans for a trendy yet subtle ensemble.
16
For a Walk in the Park
Oversize Wool Coat
An oversized wool coat worksso well for walking around the park during winter.Throw on a turtleneck and ripped jeans, and accessorize with black boots to finish it off.
17
For a Lunch Date
Eastcoast Crop Flare Washed Black High Rise Denim Jeans
Lunch dates are underrated, but you'll look absolutely swoon-worthy in a basic white turtleneck and black jeans. Finish the outfit with some eye-catching boots too!
18
For an Artsy Date
Luna Pant in Midnight Daisy
Whether you're headed to a cool art museum or going to see an experimental show, a contrasting ensemble is the way to go. Don't be afraid to mix patterns, folks.
19
For a Bar Date
Plus Size Crepe Surplice Top
Ah, the bar date. Because it's such an iconic locale, it can be extra difficult to dress for. Just don't overthink it! Stick with a cool wrap top and some trendy jeans. You can't miss.
20
For a Casual Coffee
Cedarbrook Pullover Sweater in Colorblock
Okay, so you've settled on a cute cafe to grab a latte one morning and see if there are sparks IRL, but what do you wear? Since it's super casual, a colorblock sweater and printed trousers will do just the trick.
21
For a Bougie Party
Carmel Dress
If you're heading to a more formal event—like a fancy cocktail party or even a winter wedding—go for a long-sleeve dress with a few sexy cutouts. It'll keep you warm enough without covering upeverything.
Maggie GriswoldContributing Fashion EditorMaggie Griswold (she/her) is a contributing fashion editor for Cosmopolitan and freelance writer and editor based in Los Angeles, covering everything from the latest wardrobe must-haves to interior design trends.
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