20 Winter Date Outfit Ideas for Cold Weather in 2023

Publish date: 0001-01-01

Here’s a hot take during some not-so-hot times: Winter date nights can be romantic, I promise. Indoor bars and candlelit restaurants feel charming and inviting, all while giving you the perfect excuse to cozy up to the person you're seeing (it's dark! And the music is loud! Lean in!). And now that I think about it, braving the cold for a mid-morning coffee date should honestly be re-framed as romantic in 2023. If you don’t want to leave the house, I hear you loud and clear. 

Even staying in and making a home-cooked meal is worthy of getting dressed up for at this point, so go ahead and make even the most casual weeknight meal feel a little special this season. Odds are, you haven’t had a chance to really pull out all of the sartorial stops in a while, and what better way to celebrate a good date night than with a really great outfit? 

For everyone who is celebrating their anniversaries and date nights alike at home, virtually, or on the road this season, we crafted 20 outfits that both suit a bunch of different occasions and that will keep you feeling toasty and warm all night—or day—long. Ahead, check out a bunch of cold-weather outfits that are ready for every chick-flick-approved date idea as well as a selection of all the key products to make them work for you. Use these slides solely as inspiration or pick up a few products to add some much-needed newness to your closet this season. 

 Printed Pants + White Tee  

Amp up your regular day-to-day denim looks by opting for a pair that’s covered in a little color. A white tee keeps the brightness down below feeling cool rather than over-the-top. 

Lisa Says Gah! Ellis Ankle Wide Leg Jeans

Free People One Of The Girls Henley

 Slip Dress + A Sheer Top  

Make your summer slip dress feel winter weather-ready by layering it over a long-sleeve top. If you want to show a little skin, choose a layering piece that’s on the sheerer side. 

Eliza Faulkner Pink Toni Mesh Long Sleeve Tee

Sachin & Babi Cali Satin Midi Dress

A Matching Set 

There is no easier date night-ready outfit than a coordinating set, I promise. But despite how easy it is to put together, the end result is always a winner.

Simon Miller Fine Rib Neptune Top

Simon Miller Fine Rib Saturn Pant

Blue Jeans + A White Bodysuit

When the basics are this good, why do something different? Wide or flared jeans and a tight white T-shirt (or a bodysuit) is always a good idea when heading out on a casual date. 

Marie Claire email subscribers get intel on fashion and beauty trends, hot-off-the-press celebrity news, and more. Sign up here.

MOTHER The Tomcat Roller Frayed Hem Wide Leg Jeans

Yummie Crewneck Thong Bodysuit

 A Skirt Suit 

 You’re not in the office, so why would you wear your basic work suit on a date? A matchy-matchy skirt suit looks polished but feels a little more fun. 

& Other Stories Oversized Floral Quilted Jacket

& Other Stories Quilted Floral Mini Skirt

All Black Basics + A Bright Blazer 

Instantly add some flair to your next monochromatic look by layering on a fun colored blazer. It'll be a welcome break from your usual black-on-black-on-black looks that you've been living in this season so far. 

Smyhe Classic Duchess Blazer

BLANKNYC Faux Leather Straight Leg Pant

A Blazer Dress + Lacy Tights 

If you want to channel a member of the Gossip GIrl cast on date night (but without any of the drama, of course), opt for a micro mini dress and a pair of lacy black tights. The look is half sweet half sexy in the best way. 

Natori Feather Lace Fishnet Tights

Mango Buttoned Wrap Dress

A Denim Boiler Suit + Chunky Heels 

Dress up a casual coverall with a pair of chunky heels for your next date night look. It feels both elevated and comfortable, and you won’t have to worry about keeping everything tucked in or perfectly coiffed. 

Alex Mill Standard Jumpsuit in Denim

Lafayette 148 New York Clarette Mule Sandals

A Bright Puffer + Leggings 

If it’s a casual date (as in, you’re meeting for coffee in the middle of winter) take it slow and opt for a few cold-weather essentials: A puffer and your favorite pair of black leggings. Except, swap your big black puffer coat for one that comes in a color or print that seriously stands out. 

Alo Yoga 7/8 High-Waist Airbrush Leggings

The Very Warm Unisex Hooded Puffer

A Bra Top + Trench Coat 

Stay warm and show a little skin by layering a bralette under your trench coat in lieu of an an actual shirt. A pair of casual jeans makes the revealing combo feel subdued and wearable. 

ASOS DESIGN Curve Spliced Check Trench Coat

SKIMS Jelly Sheer Bralette

A Leather Mini Dress + Knee High Boots 

Knee-high white boots are trending in a big way this season. Make the bold shoe feel modern by styling it with a chic leather (or faux-leather) mini dress for a chic date-night ensemble. 

Larroude Louise Boot In Ivory Floater

ELOQUII Faux Leather Strong Shoulder Turtleneck Mini Dress

A Slip Dress + A Cropped Cardigan 

Behold another way to make your favorite slip dress work in the winter: layering it under a cropped cardigan! This also works well if you have a really amazing cropped jacket in your collection that you love. Chunky black ankle boots add edge. 

Cuyana Silk Slip Dress

Helmut Lang Fuzzy Cardigan

Trousers + A Tank Top + A White Button Down 

I love a date night look that has serious borrowed-from-the-boys energy, and this one fits the bill. Wide-leg trousers and a fitted tank, when styled under an oversized white button-down, feel so cool.  

Derek Lam 10 Crosby Elian Utility Pants

UNIQLO Premium Linen Long-Sleeved Shirt

A Cutout Dress + An Oversized Blazer 

Cutouts are a failsafe way to show off the perfect amount of skin on a date night, but winter weather isn’t always the best time to head out without covering up.  A blazer takes care of the warmth issue while still looking great over your chosen frock. 

Zara Tailored Double Breasted Blazer

Misha Collection Bernette Dress

Baggy Jeans + A Cropped Jacket 

Baggier jeans are trending right now, and so are super-cropped jackets. Combine the two pieces for an effortless ensemble that works when the weather cools down. 

Good American Good 90s High Waist Loose Fit Nonstretch Jeans

Topshop Co-Ord Crop Vinyl Biker Jacket

A Ribbed Maxi Dress + Black Puffer Coat 

 Long live the classic black puffer! Make the winter staple work for date night wearing it over your favorite slinky ribbed maxi dress. It’s like a sweater that goes down to your toes! 

All in Favor Gathered Front Cutout Long Sleeve Rib Midi Dress

Nike Sportswear Therma-FIT City Series Jacket

A Glittery Mini Dress + Oversized Bomber Jacket 

Your next date night is a great chance to whip out your most fun mini dress. If you’re not going to a place where sparkles are necessarily commonplace, layer it under an oversized bomber jacket. 

Reformation Alisha Dress

Levis® Women's Faux Leather Dad Bomber Jacket

A Printed Sweater + Skirt

Go ahead—wear two prints at once! It works especially well if the two patterns are in the same pattern family, or if they go in the same direction, like a vertical zebra striped sweater and a polka-dotted skirt.

Wrangler Retro LS Zebra Print Sweater

The Kooples Dot Print Ruffle Maxi Skirt

Leather Trousers + A Patterned Sweater 

Leather trousers are a date-night must. They’re effortlessly cool and not always appropriate for the office, so when else do you really get a chance to wear them? A chunky sweater makes them feel a bit more toned-down. 

Rag & Bone Willow Fair Isle Wool Sweater

Commando Faux Leather Trousers

A Going Out Top + A Turtleneck 

 Do you own a top that you love to wear in the summer months but that is totally impractical for the winter? There’s an easy way to make it work: pop it over a white or black turtleneck for added warmth! 

J.Crew Tissue Turtleneck

With Jean Fasten Top

ncG1vNJzZmivp6x7rq3RopycpJGev6Z6wqikaJ6RqLWqu81onm1rYGl8qbvTZpuarJVivLbAxaKrrGWWpL9ur86lm2g%3D