Ring in Cuffing Season With These Stylish Winter Date Outfits (2024)

Table of Contents
Hutch Asymmetrical Lace Mix Slip Dress Hutch Asymmetrical Lace Mix Slip Dress Meshki Satin Halter Top - Plum Meshki Satin Halter Top - Plum Rebdolls Mia Mesh Asymmetrical Mini Bodycon Dress Rebdolls Mia Mesh Asymmetrical Mini Bodycon Dress Good American Denim Light Compression Tube Top Good American Denim Light Compression Tube Top Eloquii Leather Colorblocked Dress Eloquii Leather Colorblocked Dress Dynamite Clothing Square Neck Satin Slip Midi Dress Dynamite Clothing Square Neck Satin Slip Midi Dress Aritzia Cozy Fleece Mega Sweatpant™ Aritzia Cozy Fleece Mega Sweatpant™ Mango Knitted Turtleneck Dress Mango Knitted Turtleneck Dress Madewell Satin Maxi Slip Skirt Madewell Satin Maxi Slip Skirt H&M Rib-Knit Top with Collar H&M Rib-Knit Top with Collar Pretty Lavish Curve Collared Satin Utility Jumpsuit in Champagne Pretty Lavish Curve Collared Satin Utility Jumpsuit in Champagne Apparis Goldie Coat Apparis Goldie Coat Old Navy Sleeveless PowerSoft 7/8 Bodysuit for Women Old Navy Sleeveless PowerSoft 7/8 Bodysuit for Women Remi x Revolve Gabby Shoulder Pad Top Remi x Revolve Gabby Shoulder Pad Top Fashion to Figure Off-The-Shoulder Ruched Mesh Dress Fashion to Figure Off-The-Shoulder Ruched Mesh Dress Reformation Talia Knit Two Piece Reformation Talia Knit Two Piece By Anthropologie The Need-It Oversized Mock Neck Sweater By Anthropologie The Need-It Oversized Mock Neck Sweater & Other Stories Short-Sleeve Utility Jumpsuit & Other Stories Short-Sleeve Utility Jumpsuit Norma Kamali Diana Metallic One-Shoulder Midi-Dress Norma Kamali Diana Metallic One-Shoulder Midi-Dress ASOS DESIGN Curve Supersoft Scoop Neck Maxi Dress with Flare Sleeve ASOS DESIGN Curve Supersoft Scoop Neck Maxi Dress with Flare Sleeve FAQs References
Ring in Cuffing Season With These Stylish Winter Date Outfits (1)

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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

Ring in Cuffing Season With These Stylish Winter Date Outfits (3)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (4)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (5)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (6)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (7)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (8)

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™

Ring in Cuffing Season With These Stylish Winter Date Outfits (9)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (10)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (11)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (12)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (13)

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.

for ice skating

Apparis Goldie Coat

Ring in Cuffing Season With These Stylish Winter Date Outfits (14)

for ice skating

Apparis Goldie Coat

Now 25% Off

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (15)

for a gym date

Old Navy Sleeveless PowerSoft 7/8 Bodysuit for Women

Now 79% Off

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (16)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (17)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (18)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (19)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (20)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (21)

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

Ring in Cuffing Season With These Stylish Winter Date Outfits (22)

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.

Ring in Cuffing Season With These Stylish Winter Date Outfits (23)

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.

Ring in Cuffing Season With These Stylish Winter Date Outfits (24)

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.

Ring in Cuffing Season With These Stylish Winter Date Outfits (2024)

FAQs

What to wear on date night with husband? ›

Cute and casual date night outfits can be as basic as jeans and a graphic t-shirt to dresses and flirty sandals for the ladies. For men, jeans are most common and are easy to elevate with a crisp button-down shirt or a sport coat over a tee.

What to wear for a night out in winter? ›

Think elaborate prints, standout furs and sultry leathers that will really make an entrance on your next night out. Style yours over your favorite LBD or simply wear your coat with nothing underneath for a chicly suggestive take.

What is the best color to wear on a date? ›

When in Doubt, Wear Red or Black. According to color psychologists, the best colors to wear on a first date are red & black. Wearing the two romantic colors, especially if you're a woman, can make you appear more attractive and more desirable to your date.

What is the perfect date outfit? ›

You want your outfit to feel as laid-back as the date. "Opt for a casual, easy vibe," Priyanka says. "Keeping it low-key is the main focus." As jeans are practically the definition of casual, they're an ideal choice. "Light-wash, high-waist denim with a T-shirt is a great look and also very classic," Priyanka notes.

How to dress for a date female? ›

A midi-length dress and strappy heels are perfect for a dinner date. A strappy floral dress will go well with sandals if you are headed to a park. A casual sport fit is perfect for a sporty activity like bowling. A crop top and a pair of jean pants are perfect for a club date paired with sneakers and a sling bag.

What do you wear to a romantic night at home? ›

10 Stay at Home Date Night Outfit Ideas
  • Maxi dresses are lightweight and comfortable but still beat pajamas any day. ...
  • While leggings might be ultra-comfy, relaxed jeans look nicer but still provide the comfort of leggings. ...
  • Adding a nice blouse or a top that isn't a graphic tee shirt can do wonders.

How to look attractive in winter? ›

Dress well.

Stock up on stylish winter boots, uggs, sneakers, slippers, sweatpants, jeans, sweatshirts, leg warmers, sweaters, leggings, tights, and hats! You can even wear a dress in winter if you layer properly. Choose lightweight materials to layer so your outfit doesn't look bulky.

How do you wear stylish clothes in the winter? ›

Look for fabrics like fleece, wool, and flannel to help you stay warm.
  1. A flannel shirt worn with a pair of jeans and hiking boots is a great way to show off your rocker style even when the weather is cold.
  2. A wool sweater worn over a skirt with leggings and knee-high boots is a cute, preppy winter outfit.

What do you wear around the house when it's cold? ›

You can wear jumpers, cardigans or slipovers to keep your upper body warm. Then add a pair of trousers such as some corduroys to keep the lower part of your body warm. Finish your outfit off with a pair of thick socks, which will stop your feet from getting cold.

What color dress to wear at night? ›

When in doubt, black, gray, white, and red can work with basically any skin tone. Take the season into account when choosing a brighter or darker shade; lighter colors do well in warmer weather, while darker shades are more popular in winter.

What to wear out for dinner in 2024? ›

For formal outings, women should wear an evening gown or co*cktail dress, though casual chic, check, or leather works for informal dates. Men can't go wrong with a suit and tie, but you can dress down for a relaxed dinner with a light jacket or athleisure.

What should a 50 year old woman wear on a date winter? ›

Embrace the winter chill with a cozy yet chic sweater dress paired with knee-high boots. This combination not only keeps you warm but also exudes effortless style. For an extra touch of edge, throw on a faux leather moto jacket.

Is it harder to date in the winter? ›

Is dating harder in the winter? If you're someone who hates venturing outside in the cold and has a tendency to nest at home, it can be. Especially as our energy levels can dip and we can lack serotonin and melatonin due to fewer daylight hours, making us feel sluggish.

Are jeans OK for a first date? ›

For a Low-Key Meetup

If jeans are your comfort zone, dress up your favorite pair with a pretty puff-sleeve top and colorful mules. Great for a picnic or a low-key night on the town, this first date outfit exudes effortless confidence.

What to wear on the first date for guys in winter? ›

Men's winter first date outfits

Winter is a time to layer up, but this doesn't have to mean style comes second. If you're meeting for a daytime date, perhaps a trip to a food market or a crisp walk, start with a pair of jeans and layer a crew neck jumper over a long-sleeved shirt.

References

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