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

Snuggle up.

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? It's frightful. Our collective holiday cheer? It's likely left the building. The desire to get all dressed up? It's likely to dissipate after the clock strikes midnight on New Year's Eve. Basically, 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, even if said thing is as simple as a night out. With colder temperatures, it's so easy to fall into a rut where you only binge-watch shows on Netflix (no shade), 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. But 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. 

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

Allow us to introduce you to the perfect day-to-night dress. 

These cobalt blue tights are sure to make all your winter ensembles ten times cooler. 

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 mini skirt can be cold-weather friendly by being paired with a shearling coat, turtleneck, thermal tights, and knee-high boots. 

You'll be so cozy in this coat. 

Insider trick: you can make them realize you have great legs by wearing knee-high boots. 

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

Tank tops are seasonless. 

White leather pants? We love to see it. 

Let's be honest; 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, fur coat, and knee-high boots. It's a look that requires minimal effort but will have a maximal impact on your date. 

Colder temperatures won't have anything on you in this coat. 

Trust us, you can't survive the winter without Uniqlo's thermal leggings. 

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 toy the line between being chic and cozy—e.g., an oversized faux fur coat. When in doubt, pairing this outerwear with a little black dress, tights, pumps, and a shoulder bag will ensure you look great (and feel that way too). 

Rich energy, embodied. 

Excuse us, we must spend the rest of the day staring at these Saint Laurent shoes. 

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). 

A guaranted compliment magnet. 

We love the chocolate brown hue of these tights. 

If it's unclear by now, 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—e.g., pair it with a turtleneck, a moto jacket, and even layer thermal pieces underneath for extra warmth. 

You'll look effortlessly cool in this jacket. 

You can dress this skirt up or down. 

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. 

Sublime, indeed. 

What's great about this skirt is that you can also wear it again to work after your date night. 

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 mini skirt, 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, sweater, knee-high boots, and statement earrings. 

Wait, until you see the matching mini skirt ($125). 

These are sure to spark a conversation. 

We've all had those moments where we want to wear something a bit more risqué for date night—ahem, 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. 

Perfect for layering. 

You won't ever regret investing in a great pair of trousers. 

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 oversized t-shirt and crewneck sweater over your item. Finish off the look by drawing attention to the sheer bottom by wearing cute slingback heels. 

Cozy, cozy, cozy. 

Buckle up, baby! 

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 catsuit with a leather blazer. 

Leather blazers are a must-have for the winter. 

They won't be able to keep their eyes off you. 

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 oversized button-down or layered knitwear (as seen in Miu Miu's F/W 23 show) on top. 

You'll get so much wear out of this shirt long past date night. 

Pulling off the hot pant trend has never been easier thanks to this legging. 

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 fail-proof way to shine all evening long sans wardrobe mishaps. 

Cashmere is always a good idea. 

How fun is this sequin skirt though? 

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 bags) 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. 

For dates furing the evening, it's essential to have a warm coat. 

Hot, hot, hot. 

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

These earrings are at the top of our wishlists right now. 

Don't worry, it comes in black too! 

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. 

So pretty. 

When in doubt, opting for relaxed denim for an upcoming date is failproof. 

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. 

It doesn't get more sultry than a little off-the-shoulder moment. 

It's big enough to fit the essentials, without being capaciously large for a night out. 

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. But 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. 

Our editors love Leset's tees. 

Don't be afraid to shop a denim skirt with a front slit so you can show off your legs. 

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 towards 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. 

You'll look so elegant in this trench coat. 

Give off the appearance you mean business with a structured bag. 

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. 

We can attest to this skirt being the coziest thing you could add to your closet. 

Metallic shoes are still trending, btw. 

In addition to relying on matching sets, other styling hacks can make you look elegant with little effort. Chief among them? Incorporating one to two statement pieces. Nothing can make those  "boring" wardrobe staples (e.g., t-shirts, leather skirts, and so on) 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. 

There's no doubt that you'll catch their attention in this coat. 

If a pair of boots embodied the song "Maneater" by Nelly Furtado, it would surely be this pair. 

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 colorblocking. 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. 

If you're prone to cold spells try layering underneath or above this sweater. 

You can shop this in 12 other colorways, including black, navy, and paprika. 

Congratulations, you've made it to the end of this story! Hopefully by now, you feel like you have an idea of what to wear for a date during the winter. But should you need one last nugget of parting wisdom let it be this: simplicity is key. When in doubt, a colorful sweater dress paired with neutral accessories will win over their heart everytime. 

It's love at first sight. 

Stretchy headbands are trending with the style set again. 

from Who What Wear