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Here's the cool thing about dates—they shall go on! And in every and any season! But I can totally get why you think it could be the absolute worst in the wintertime, bb. 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. Yes, even for those times you're a wedding date or if you've got yourself a Valentine this year! From casual, low-key vibes to bougie lewks that’ll knock your date’s socks off, we’ve compiled 25 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!
for a co*cktail date
Hutch Asymmetrical Lace Mix Slip Dress
for a co*cktail date
Hutch Asymmetrical Lace Mix Slip Dress
This gorge, lace slip dress is the perf mix of "I'm into you" and "let's see where this goes..."
for a dinner in the city
Meshki Satin Halter Top - Plum
for a dinner in the city
Meshki Satin Halter Top - Plum
Pretty sure they'll be absolutely infatuated with ya when you show up in this halter top and ruched maxi skirt.
for a bar date
Rebdolls Mia Mesh Asymmetrical Mini Bodycon 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 asymmetrical bodycon dress. If you’re meeting up for co*cktails at an upscale bar, a martini glass makes a great accessory to this number.
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for a low-key date
Good American Denim Light Compression Tube Top
for a low-key date
Good American Denim Light Compression Tube Top
Frankly, you can’t go wrong with an all-denim look. It’s a combo that’ll stand the test of time—and it looks really, really cute.
for a post-work date
Eloquii Leather Colorblocked Dress
for a post-work date
Eloquii Leather Colorblocked Dress
Now 42% Off
A leather colorblocked dress says you're a stylish boss in-and-out the office. You won’t seem overdressed, and there’s no need to worry about bringing extra clothes to work.
for a glass of wine
Dynamite Clothing Square Neck Satin Slip Midi Dress
for a glass of wine
Dynamite Clothing Square Neck Satin Slip Midi Dress
Now 60% Off
A slip dress is always a good move! Plus, you can throw on a pair of tights and a slouchy sweater for more warmth if needed.
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for a walk in the park
Aritzia Cozy Fleece Mega Sweatpant™
for a walk in the park
Aritzia Cozy Fleece Mega Sweatpant™
Takin' a stroll with your boo thang? You'll be absolutely adorbs in this super-cute boyfriend hoodie and sweatpants made of fleece.
for a day trip
Mango Knitted Turtleneck Dress
for a day trip
Mango Knitted Turtleneck Dress
The best part about long dresses is that they can be a part of your wardrobe all year round. Pair this turtleneck one with a tan coat and chunky boots, and you’ll be comfy but cute for any travel plans.
for meeting the family
Madewell Satin Maxi Slip Skirt
for meeting the family
Madewell Satin Maxi Slip Skirt
Meeting the fam? This is the perf Sunday brunch 'fit to show your sweet side.
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for a coffee date
H&M Rib-Knit Top with Collar
for a coffee date
H&M Rib-Knit Top with Collar
Head to a coffee shop on your lunch date in this easy look.
for meeting their friends
Pretty Lavish Curve Collared Satin Utility Jumpsuit in Champagne
for meeting their friends
Pretty Lavish Curve Collared Satin Utility Jumpsuit in Champagne
Now 60% Off
No idea what to wear to meet the homies? Jumpsuits are instant lifesavers, especially this utility-styled one made of satin.
Want to wear something more unique? Opt for a bold, hooded coat to really make an impression on (and off!) the ice. Wear a turtleneck and black pants for a trendy yet subtle ensemble.
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for a gym date
Old Navy Sleeveless PowerSoft 7/8 Bodysuit for Women
Do you even lift? Show how much you do (or don't) know at the gym with this highly-rated, glossy bodysuit.
for an upscale party
Remi x Revolve Gabby Shoulder Pad Top
for an upscale party
Remi x Revolve Gabby Shoulder Pad Top
Show that you're a whole vibe in sparkly number that includes a crop top with shoulder pads and a maxi skirt with a slit.
for a concert date
Fashion to Figure Off-The-Shoulder Ruched Mesh Dress
for a concert date
Fashion to Figure Off-The-Shoulder Ruched Mesh Dress
The pop of neon green is perf for a concert date. Who cares about what your date thinks atp? Beyonce would be pleased.
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for a jazzy night
Reformation Talia Knit Two Piece
for a jazzy night
Reformation Talia Knit Two Piece
This two-piece knit look is giving effortlessly chic! The jazz club won't know what hit them, tbh.
for a library date
By Anthropologie The Need-It Oversized Mock Neck Sweater
for a library date
By Anthropologie The Need-It Oversized Mock Neck Sweater
Oh hey scholar, you will look super studious in this mock neck sweater, tiered skirt, and socks with sandals.
for a museum date
& Other Stories Short-Sleeve Utility Jumpsuit
for a museum date
& Other Stories Short-Sleeve Utility Jumpsuit
Take in beautiful art with a jumpsuit, lil red bag, and black booties.
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for a candlelit dinner
Norma Kamali Diana Metallic One-Shoulder Midi-Dress
for a candlelit dinner
Norma Kamali Diana Metallic One-Shoulder Midi-Dress
If it’s a fancier occasion like dinner and drinks, a metallic midi dress will make you feel confident for the night ahead. Throw on a stylish faux-fur coat and strappy heels to dress it up even further.
for an anything-goes date
ASOS DESIGN Curve Supersoft Scoop Neck Maxi Dress with Flare Sleeve
for an anything-goes date
ASOS DESIGN Curve Supersoft Scoop Neck Maxi Dress with Flare Sleeve
Reviewers are raving about the soft material and the bell sleeves—your date will rave about you.
Maggie Griswold
Contributing Fashion Editor
Maggie 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. Along with Cosmopolitan, you can find her work on Oprah Daily, StyleCaster, Women's Health, and House Digest, among others. She's a big (read: ridiculously huge) fan of the '90s sitcom Frasier, all things Shakespeare, and a good romance-filled YA novel. Follow her on Instagram.
Tarah-Lynn Saint-Elien
Fashion Editor
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.com almost 10 years ago. Since then, she's also served as the style editor at The Haitian Times. The Haitian-American pageant queen is a Syracuse Masters graduate and the author of two books, including: Claim Your Crown. Follow her on Instagram and Twitter: @iamtarahlynn.
