Baby, It's Cold Outside! 24 Date-Night Outfits You Can Actually Wear in Winter


It's time to be honest. The whole idea that this is the most wonderful time of the year is a bit overhyped. Don't get us wrong. Some things are wonderful about the holiday season, but once you get past all of the festivities, you realize that it's a bit dark—literally and figuratively. After all, the weather outside is frightful. Our collective holiday cheer has likely left the building, and the desire to get all dressed up dissipates after the clock strikes midnight on New Year's Day. The wintertime can be challenging, even for those who love this time of year. 

It's only natural then that we'd have to find ways to cultivate tiny pockets of joy. Enter date night into the chat. As silly as it might seem, having something to look forward to in these colder months is a saving grace. With colder temperatures, it's so easy to fall into a rut where you only binge-watch shows on Netflix, but we implore you to plan a date night! There's no better way to beat your winter blues back than by slipping into a stylish outfit to spend the evening with your special someone.

If you find the prospect of choosing what to wear for a date in the winter debilitating, don't fret. Ahead, we're sharing 24 winter date-night outfit ideas from fashion people that will make putting together an elegant look effortlessly. Whether you're dipping your toes back into the dating pool or need an excuse to get your partner off the couch, these looks will motivate you to get back out there despite the cold temperatures. 


Hoops + Black Dress + Clutch Bag + Colorful Tights + Pointed Pumps
(Image credit: @sintijaselicka)

What's one of the simplest ways to make a little black dress work for colder weather? Layering tights underneath. Time and again, this pairing works for date night. If you want to make the formula feel fresher, opt for colorful hosiery, pointed pumps, and a clutch bag. 

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Shearling Jacket + Turtleneck + Miniskirt + Tights + Knee-High Boots
(Image credit: @emmanuellek_)

Repeat after us: Layering is key. By no means do you have to be fully covered (unless that's your thing). Instead, you have to get creative with how you style date-night staples. For example, the classic miniskirt can be cold weather–friendly when paired with a shearling coat, a turtleneck, thermal tights, and knee-high boots. 

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Hoops + Shaggy Fur Coat + Tank Top + Leather Trousers + Handbag + Thong Sandals
(Image credit: @emnitta)

Just because it's the dead of winter doesn't mean you "must" relinquish colors typically associated with the summertime. You can transition this neutral into the winter by opting for pieces adept for the weather. For example, try styling your favorite white tank top with matching leather pants and a shaggy fur coat for a look that's winter-ready. 

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Sunglasses + Shaggy Fur Coat + Sweater + Handbag + Thermal Leggings + Knee-High Boots
(Image credit: @nlmarilyn)

Sometimes, it's so cold outside you're not compelled to try to slip into leather pants. But who said you had to ditch your cozy essentials? Instead of taking off your thermal leggings, dress them up by styling them with a sweater, a fur coat, and knee-high boots. It's a look that requires minimal effort but will have a maximal impact on your date. 

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Headband + Fur Coat + Minidress + Tights + Slingback Heels + Shoulder Bag
(Image credit: @nitsanraiter)

Not to sound like a broken record, but the key to mastering dressing well during the wintertime comes down to having solid essentials. You don't have to reinvent the wheel. You just need items that can toe the line between being chic and cozy—e.g., an oversize faux-fur coat. When in doubt, pairing this outerwear with a little black dress, tights, pumps, and a shoulder bag will ensure you look and feel great.

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Leather Bomber Jacket + Asymmetrical Minidress + Tights + Slingbacks
(Image credit: @oumaymaboumeshouli)

Are you still in denial about the fact we're in the dead of winter? We get it. Packing away the warm-weather items is hard, especially if you have a killer collection of dresses. Rather than ditching your signature white frock, try winterizing it by styling it with a leather bomber jacket, thermal tights, and slingback pumps or boots. 

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Earrings + Turtleneck + Moto Jacket + Maxi Slip Skirt + Pointed Pumps
(Image credit: @lefevrediary)

If it's still unclear, let us set the record straight. Any piece can be worn in the winter if styled right. The quintessential slip skirts that the fashion set relies on for date night during warmer seasons work for the winter too. You have to be creative with the styling—pair it with a turtleneck and a moto jacket, and even layer thermal pieces underneath for extra warmth. 

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Clip-On Earrings + Scoop-Neck Tank + Belt + Leather Skirt + Tights + Ankle-Strap Pumps + Clutch
(Image credit: @iziangus)

For anyone who resides in warmer climates, it can be equally challenging to choose the right outfit for date night. While you won't necessarily need as many layers, you still want your look to feel seasonal—enter the outfit above. Style a low-cut silk tank top with a leather skirt, sheer tights, and ankle-strap pumps for a look that's sure to send a chill down their spine. 

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Sculptural Earrings + Leather Moto Jacket + Matching Miniskirt + Knee-High Boots
(Image credit: @daniellejinadu)

Another way you can find the balance between choosing a date-night look that's weather-friendly and sure to "wow" them is by paying attention to textiles. For instance, you can still wear a miniskirt, but rather than one made from cotton or polyester, opt for one made with leather. Additionally, you can make the look more functional and fashionable by pairing it with a matching leather jacket, a sweater, knee-high boots, and statement earrings. 

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Long Coat + Sheer Dress + Trousers + Pointed Ankle Boots + Shoulder Bag
(Image credit: @amalie_gassmann)

We've all had those moments where we want to wear something a bit more risqué for date night—a sheer dress, for example—but the weather isn't complying. Rather than covering up entirely, why not get creative with your layering? You can still wear your sheer dress or top without freezing by styling it with trousers, a wool coat, and ankle boots. 

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Sheer Slip Skirt + T-Shirt + Crewneck Sweater + Slingbacks
(Image credit: @_jeanettemadsen_)

Oh, you thought trousers were the only way you could make sheer separates winter-ready? Think again. For readers looking to make a sheer slip skirt or dress warmer, take inspiration from the look above and pair your piece with an oversize T-shirt and crewneck sweater. Finish off the look by drawing attention to the sheer bottom by wearing cute slingback heels. 

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Sculptural Earrings + Leather Blazer + Lace Jumpsuit + Heels
(Image credit: @coco_floflo)

If you love the idea of wearing a semi-sheer look but want to be fully covered, then the outfit above is all you. You get the best of both worlds by opting for a lace jumpsuit with a leather blazer. 

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Oversize Button-Down + Belt + Hot Pants + Tights + Sandals
(Image credit: @emilisindlev)

In addition to wearing sheer pieces, you can show off a tiny bit of skin by wearing one of the biggest trends of the moment: hot pants. While the idea of micro-shorts or briefs during the dead of winter might seem like a bad idea, the outfit above proves otherwise. You can make this item work for cold weather by layering thermal tights underneath along with an oversize button-down or layered knitwear (as seen in Miu Miu's F/W 23 show) on top. 

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Hoops + Crewneck Sweater + Sequin Skirt + Slingbacks
(Image credit: @abimarvel)

It's understandable if you do not want to get too adventurous with your styling for an upcoming date. After all, you want to wear something comfortable! But if you still want to have the feeling of wearing something "shiny and new" without taking too much risk, the outfit idea above is right up your alley. Pairing a sequin skirt of any length with a crewneck sweater and slingback heels is a failproof way to shine all evening long sans wardrobe mishaps. 

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Maxi Coat + Minidress + Scarf + Sheer Tights + Knee-High Boots + Woven Bag + Gloves
(Image credit: @ingridedvinsen )

When it's far too cold to be bothered about wearing anything too revealing, you'll want to shift the focus when crafting your date-night outfit. Rather than showing the most skin, a simple way you can add instant visual intrigue is by opting for accessories (e.g., boots or a bag) in contrasting neutral hues compared to the rest of your outfit. For example, an all-black outfit like the one above is a bit spicer with the addition of chocolate-brown knee-high boots and a woven handbag. 

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Earrings + Off-the-Shoulder Sweaterdress + Handbag + Knee-High Boots
(Image credit: @rabialafashionista)

What's another simple but stylish date-night outfit formula you can rely on every time? The sweaterdress. But you don't want to just wear any old frumpy knit. Instead, opt for a formfitting off-the-shoulder sweaterdress to bring a bit of heat to the evening. Additionally, if you style it with oversize earrings, you'll draw additional attention to the neckline, which is a win in our books. 

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Sculptural Earrings + Bustier + Baggy Jeans + Handbag + Pointed Pumps
(Image credit: @iliridakrasniqi)

Not the biggest fan of dresses? Don't fret. There's another simple formula you can rely on to look stylish for the evening—see above! Pairing a bustier top with baggy jeans, heels, statement earrings, and a small handbag works every single time. 

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Hoops + Sweater + Wide-Leg Jeans + Pointed Pumps + Shoulder Bag
(Image credit: @slipintostyle)

Should the temperatures not allow you to get away with wearing a bustier top out for the evening, swap the piece out with an off-the-shoulder sweater for a look that's just as flattering. 

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Fur Coat + T-Shirt + Denim Maxi Skirt + Tights + Pumps
(Image credit: @sylviemus_)

When you're not in the mood to wear a chunky knitted sweater or a risqué bustier, then the T-shirt is the next best option. If you're worried about this top being a bit too casual for date night, you'll want to look to the French fashion set for guidance. Pair your T-shirt with a denim maxi skirt, pointed pumps, and a faux-fur coat for an effortlessly chic look. 

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Earrings + Leather Coat + Turtleneck + Maxi Slip Skirt + Wedges + Handbag
(Image credit: @thecarolinelin)

You'll want to do some minor swaps if your evening plans call for something a bit more formal than denim and tees. Take inspiration from the ease of the former look, but aspire toward the minimalism of the outfit above. Swap out your denim skirt for a maxi slip skirt, your T-shirt for a turtleneck, and your faux fur coat for a leather trench coat for a look that's still easy but far more elevated. 

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Sunglasses + Earrings + Sweater + Matching Knit Skirt + Pumps + Handbag
(Image credit: @haaannajohansson)

One more easy but elegant outfit formula you can turn to for date night is the matching knit set. When you're stressed about what to wear, nothing is going to be more effortless than throwing on a chic knit top with a matching skirt, pumps, and a handbag. 

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Colorful Wool Coat + T-Shirt + Leather Skirt + Snakeskin Boots + Handbag
(Image credit: @sobalera)

In addition to relying on matching sets, other styling hacks can make you look elegant with little effort. Chief among them is incorporating one to two statement pieces. Nothing can make those "boring" wardrobe staples feel bold again quite like the addition of fun outerwear, footwear, or both. When in doubt, the addition of a colorful coat or pair of animal-print boots can surely make any outfit feel date night ready. 

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Long Scarf + Sweater + Slip Skirt + Tights + Pointed Pumps
(Image credit: @dawn.tan)

Are you averse to statement pieces? You don't have to go the maximalist route to make a lasting impression on your date. In fact, a more minimal way to make staples feel special is by taking inspiration from the look above by playing with color-blocking. Pick two to three neutral hues to style together through various separates—albeit in the form of a sweater and slip skirt or blouse and trousers—to make a more subtle statement. 

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Headband + Clip-On Earrings + Sunglasses + Sweaterdress + Clutch + Pointed Pumps
(Image credit: @bettinalooney)

Congratulations, you've made it to the end of this story! Hopefully, you feel like you have an idea of what to wear for a date during the winter. Should you need one last nugget of parting wisdom let it be this: Simplicity is key. When in doubt, a colorful sweaterdress paired with neutral accessories will win their heart every time. 

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