23 Winter Date Outfits To Heat Up Your Next Night Out

It may be cold, but you can still melt some hearts.

winter dresses

Free People / Unsplash

Winter is here, but it doesn’t mean that our love lives are slowing down at all. While cold temperatures and unpredictable weather (especially if you live somewhere with snow) are not the most ideal conditions for a date night, there are still plenty of ways to have memorable looks for your dates this season. Whether you’re going on a first date or celebrating with your cuffing partner, below you'll find 23 winter date outfits that will heat up even the coldest nights.

Building a Snowman 

Do you want to build a snowman? If you live in an area with plenty of snow, building a snowman (or your own snow couple) is a lovely, cheap date night idea that allows you to have some stress-free fun. Put on your favorite overalls, a warm shirt, a jacket, and most importantly, have fun.

Going to the Theater 

The theater is a lovely date night activity that lets you get all dressed up without spending much time out in the cold. Pair some over-the-knee boots with a stunning blazer dress to create a dramatic look to match whatever show you're seeing.

Looking at Holiday Lights

Early winter brings plenty of festive activities that you can do with your date for free. After dinner or a holiday activity, walk around the neighborhood and check out the lights on display. Keep it casual with a cheery sweater, scarf, and some jeans. 

New Year's Eve Party

Personally, we can’t think of a better date night activity than ringing in the new year. Pull out all the stops with a dazzling holiday party outfit complete with sequins and glitter—you'll look radiant as the clock strikes midnight. 

 Going Sledding

Indulge in some childhood nostalgia with an impromptu sledding date on the next snowy day. Grab your coat, boots, and sled to spend the day in an outfit that totally sleighs (we had to).

Hot Chocolate Date 

Melt those first date jitters away with hot chocolate this winter. It’s a perfect way to meet someone in a casual setting, so keep your outfit low-key with a cutout turtleneck and a knit skirt for a cozy date look.

Cozy Movie Night 

Netflix and chill is a time-honored tradition during cuffing season. Elevate your winter date outfit with a cozy lounge set, some slippers, and a robe to set the mood, no matter what you’re watching (or not watching).

Ice Skating 

The classic winter date idea, going ice skating is a great way to show off your moves (all those years of watching Ice Princess are finally paying off), or an excuse to hold onto your partner on the ice. Wear something functional, like a lacy top, jeans, and a cheerful coat.

Winter Hike 

Don’t hang up your hiking boots just because the temperature is dropping—you can still get some beautiful, scenic adventures in during the winter months. Just grab a puffer jacket and some boots and you’re ready to explore.

Chilling at the Ski Lodge 

Whether you’re on the slopes or spending time in the lodge, a day or weekend at ski resorts is the perfect way to spend a winter date. Grab a cute ski suit and look just like Lady Gaga in House of Gucci.

Wine Tasting 

While there’s never a bad time to go tasting, winter is a great time to check out your local wineries for mulled cider or to sample their latest blends. A satin blouse with leather pants is both sophisticated and fun.

Paint and Sip 

Staying inside because of the weather is the perfect opportunity for you and your date to practice your artist skills. Go on a paint-and-sip date, either at home or taking an actual class, to have some fun. A cute jumper dress and sweater combination can help you embrace your inner artist.

Board Game Night 

If a snowstorm cancels your plans, stay in and play some of your favorite board games for a fun date night. Whether it’s just the two of you or a group date, look sharp with a sweater vest and pants as you crush the competition at trivia.

Museum Date 

Get away from the cold weather by spending the day getting lost in the museum. You’ll look like a piece of art in a fringe skirt, a cropped top, and some artistic earrings.

Dance Class 

Do something that gets you moving while building physical and emotional connection by taking a dance class. A slip dress, a mesh turtleneck, and some comfortable shoes with have you tangoing the night away.

Baking Cookies

After watching every season of The Great British Bake Off together, you’re ready to take what you learn into the kitchen and make some sweet treats together. Create some cozy vibes with a thick sweater over a dress for a cottagecore vibe.

Carriage Ride 

Explore your city in a new way by taking a carriage ride. Get all cozy with some hot chocolate or egg nog as you let the carriage whisk you away. Stand out in a winter white outfit that will put the snow to shame.

Bowling Night

Get out of the house and spend the night in the lanes this winter. This classic date activity calls for a classic outfit like a dress, matching tights, and a striking bag.

Weekend Getaway 

Escape your everyday life by going away for the weekend. Spending time with your partner in a cute bed and breakfast is the perfect way to make love bloom—especially with a sweet dress and a few accessories.

Hometown Tourist 

Play tourist in your hometown by exploring it with your date, especially if they are new to the area. Check out all the tourist attractions and stay warm with a long coat and turtleneck dress. Make sure you have good shoes for walking.

Hockey Game 

Go sports! Whether you’re a major hockey fan or new to the game, get on the action by going to a game with your date. Put on your varsity jacket and some jeans and you’re ready to cheer.

Brunch Date 

If you’re sick of the typical dinner dates, try going out to brunch instead. Throw on a sweater dress, a chain belt, and your favorite boots and you’re ready for romance.

Fondue Night 

Go retro with a '70s-inspired fondue night date. If you'd like, you and your date can get a little cheesy by feeding each other snacks on a stick. Dress it up with a fun suede skirt and bodysuit to play with the retro vibe.

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