The 20 Best Winter Date Outfits, Cold Be Damned

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. 

 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. 

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.

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. 

 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. 

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. 

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. 

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. 

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. 

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. 

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. 

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. 

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.  

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. 

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. 

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! 

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. 

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.

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. 

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!