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  • Megan Watkins

Winter Date Ideas

The holiday season can be stressful! So, sometimes it's nice to destress and spend some quality time with your partner doing something fun. Whether you're staying in or going out, just to spend some time together can help to shake off some of that stress this time of year.

So, we've made a list of some date ideas for this special time of the year and put together potential outfits for our ladies to wear on these dates! Make plans or be spontaneous but spend some time together and have fun!



One of the most classic and fun winter activities for couples is ice skating! It seems like every Christmas movie features ice-skating at some point. Whether you're a master of the rink or barely able to stand up straight, it'll be a fun date! You can bond over how clumsy you both may be and help each other up when you fall and have a good laugh. Dare each other to try classic ice-skating moves like a turn or a jump. Seriously, is there anything cuter than gliding on the ice rink hand in hand? When you're all skated-out, you can head to a local cafe or home for some nice hot chocolate!

An outfit for this date can but casual, but still cute! Some skinny jeans and a cute sweater list this fit would be perfect! The booties just pull the whole outfit together!


Holiday Movie Marathon and Treats

This is one of those winter activities couples usually do without thinking. After all, who doesn’t love a good movie marathon? Plus, there's something about watching them during the holiday season that gets you all excited about the gifts you'll open soon. Cozy up on the couch with a fresh batch of popcorn and some holiday treats. See our treat and movie ideas below!

Holiday Treat Ideas

Christmas Cookies


Candy Canes

Oreo Balls

Chocolate Chip Cookies


Hot Chocolate

Chocolate Covered Pretzels

Festive Ice Crean Sundaes

Cinnamon Rolls

And More!

Christmas Movie Ideas

How The Grinch Stole Christmas


Home Alone

A Christmas Carol

It's a Wonderful Life

Christmas Vacation

Tim Allen's: The Santa Claus

The Polar Express

Christmas With the Kranks

Miracle on 34th Street

And More!

For this cozy date, something comfortable is best! This Barbour 2-piece set would be the perfect fit to lounge in and watch movies all day! These pink On Shoes will complete the fit if you need to run to the store for some goodies!


Gingerbread Houses

It’s that time of year when you can get away with fun activities like making a gingerbread house together! Building a gingerbread house is a classic winter staple. You can make the cookies from scratch, but we won't judge if you use a store-bought kit with pre-made gingerbread. The important part is construction—make your house a home with frosted window dressings and candy decorations for the yard. If it happens to turn into a frosting fight… so be it! You both might be a bit of a sugar high from eating all that candy, but no doubt you’ll finish with a masterpiece to put on display for all to see.

Spending a date building gingerbread houses is a cozy, at-home activity for the two of you. So, something comfy is exactly what you should wear. It can definitely be cute too though, since you'll be taking pictures of your little houses when you're done! This 3-piece fit is the perfect thing to wear, it's comfortable and cute!


Christmas Festival

If you're lucky enough to live in somewhere that holds Christmas festivals, you might be treated to incredible sights and activities. Festivals are events where you celebrate together, so use that for both of you to feel the joy and celebration. Check out the booths, try some food and treats, and have fun! Moments like these are ones you never forget.

Going out to a Christmas Festival is the perfect opportunity to break out those festive colors! This red shirt is absolutely the perfect top to wear with some distressed jeans. This date can involve a lot of walking and standing, so you can the outfit up with some booties or some cute flats!


Christmas Shopping

The holidays are approaching, and winter date idea that’s both fun and practical is Christmas shopping together! Head to the mall or your favorite stores or boutiques to browse together and start crossing off those must-haves on your holiday wish lists. You can use the outing to drop hints to your partner about what you both really want for the holidays, too.

Christmas shopping is a simple outing that you can dress casual for. This fringy gray sweater and matching Hey Dudes is the perfect look for shopping! Throw on some distressed jeans with it and you are ready to take on those Christmas lists! And don't forget your favorite clutch purse!


Christmas Lights

How well do you know your respective neighborhood? Every town has that one street decked out in holiday lights, so why not take a scenic drive with your partner and admire all the hard work that went into your neighbors' displays?

If you don't live in a neighborhood or you want to see different light displays, pack into the car for this free winter date night idea that’s sure to dazzle! Check for maps in your local newspapers to make sure you hit all the best displays in your area.

We all know that it can get chilly on those winter nights, the perfect time to go see the Christmas lights! So, an oversized sweater and leggings are the perfect way to stay warm, even if you are just driving around to look at the lights. Grab your Dolce Vita booties and you're ready to admire some pretty lights!


Christmas Party

The holidays are the perfect season for dressing up. There is like a Christmas party with all your friends! So, get dressed up together and head to a friend's party, or host your own and invite all your favorite people over for some holiday fun!

A Christmas party is a great opportunity to break out your favorite snazzy outfit! This black and white cropped top and some black flares are the perfect way to party in style! Complete the fit with some black booties and it's time to party!!


Wine Tasting

You can check out wine tastings in your area. Try the boldest reds, the sweetest whites, and everything in between! Choose a winery that has some live music going on. It can be a fun way to broaden your taste!

If you don't want you go wine tasting, try a brewery instead!

Or if she likes wine and he likes beer, why not do both?!

This classy little date calls for a cute outfit! These burgundy leather pants and this blouse is too cute not to go tasting in! Slip on some heeled mules and drink up!


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