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8 Winter Date Ideas (and What to Wear on Them)

November 22, 2019 | Filed in: Your Closet

As we enter the dark, cold, and long winter, it makes sense that we’d want to cuddle up and hibernate as much as possible. Why venture out into the tundra when you can stay inside wrapped in blankets, binge watching the latest season of The Crown? Well, here’s a good reason: We put together eight great winter date and outfit combos, and you’re missing out on them by hiding under the covers! Try them out on your next date night. We’re positive you and your Mr. or Mrs. Claus will have a jolly ol’ time. 

Go Around and See the Lights

Let’s start off with something traditional. Whether you head out on foot, or step into a car and drive around your town’s big Christmas lights district (every town has one!), pick up some hot cocoa on the way for extra warm fuzzies and make sure to wear something special. Top the Lenox skirt with the Ismelka top, and you’ll look like a woman who gets down with a little whimsy.

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Enjoy Some Chicken Parm

Apparently the Italian classic is the haute cuisine of the dating world right now—and there’s no better season to enjoy this cheesy dish (though we definitely eat it year-round). Dress a little festively for this old-school date night by pairing the Zhou culotte in topaz with the Ava top and a pair of sparkly earrings

Take a Cocktail Class

Sure, you could dip into a cozy bar for a drink, but why not learn how to make your own? Look for a cocktail class in your area, and make a night of it. Wear the Gosia dress, so you can roll up your sleeves and get dirty (if the occasion arises). Bonus: it’s machine-washable, should you spill your negroni. 

Have a Phone-Free Adventure

What if you went out and didn’t bring your phones? We dare you! Make a game plan that involves heading somewhere new, and let your sense of direction and adventure guide you. Just make sure to snap a pic of your outfit ahead of time, because you’ll want evidence of how chic you look. For this expedition, we recommend the Zora top with the Logan skirt and the Lana boot

Plan a Getaway

Really can’t stand the cold? We get it. Why not tuck into a little booth somewhere and plan your next vacation? If your relationship is new, there’s no better way to test it (in a fun way!) than taking a trip together. Stay comfy in the Darby sweater and the Mejia pant so you can focus on the logistics. Paris for St. Patrick’s Day? Why not!

Finally Get That Reservation

We all have that one restaurant we’ve been dying to go to that’s also impossible to get into. This is your friendly reminder to try to book a table now. Even if it’s three months from today, you’ll have something on your calendar to look forward to when the winter season starts to get really bleak. As for what you’ll wear on the big night—why not try the Carmen jacket over the Jane dress, cinched with the Beebe belt? Yup, outfit planning really can be the easy part.  

Day at the Museum

Not all dates have to take place in the evening. Get some vitamin D and head out for a little gallery hop or museum crawl. Make sure to enjoy croissants, coffee, and whatever else you want along the way. You’ll feel extra fancy while wearing the Nancy sweater, the Surrey skirt, and the Westbury earrings

Keep It Cute and Cheesy

…Or you could just stay in and have a fondue party. But try to make it special by keeping your soft pants at bay. Instead, opt for the next best thing—the Elliot trouser, the Choe top, and the Leigh cardigan.


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Caitlin Abber is the Brand Editor at M.M. LaFleur, and an award-winning writer and content creator. Over the last decade she has held senior editorial positions at MTV, Women's Health, Public Radio International, and Bustle, and has bylines at InStyle and OprahMag.com. Read more of Caitlin's posts.


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