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15 Winter Date Night Outfits That are Both Cute and Practical

If there’s one thing I look forward to at the end of a long work week, it’s a date night with my husband. Grabbing a cocktail, indulging in a good meal, and unwinding at a restaurant that has a fun atmosphere just has a way of resetting everything. And even in the winter (when the weather can be unruly), we still try to be mindful about scoring some one-on-one time together.

While we spend the bulk of our winter in Miami, we still have weeks that we spend either in Brooklyn or traveling to Aspen, which are two places that obviously come with much cooler climates.

I’ll admit that a winter date night isn’t always the easiest to get ready for—you want to be warm but also don’t want to look like a triple-layered, bundled up snowman. And don’t even get me started on the snow, which can really be a challenge to dress for.

I know that finding the perfect outfit for a date night in cold weather can be frustrating, but the good news is that it’s definitely possible to look cute while staying cozy at the same time. Here, I’m sharing a roundup of outfits you can wear on your next winter date night, whether you’re grabbing dinner, going ice skating, or heading to an event.

15 Best Winter Date Night Outfits

Oversized Coat + Leather Leggings + Ankle Boots

If you’ve been reading my blog for a while now, you likely know that my love for leather leggings runs deep. They’re the perfect staple to wear throughout the winter because they keep you warm, go with everything, and they look adorable for a variety of occasions.

Pair them with a sweater, oversized coat, and some boots for a simple, date night-ready look.

Oversized Coat + Leather Leggings + Ankle Boots

Bodysuit + Leather Pants + Boots

Winter white outfits are certainly a thing, but I also love to wear all-black throughout this season. Wearing one cohesive color creates such an elevated look, but in reality, it’s super easy to throw together with pieces you likely have in your closet already.

For this particular outfit, I went with wide leg leather pants and ankle boots, but you could also wear leather leggings and over-the-knee boots (these are my favorite pair!)

Bodysuit + Leather Pants Winter Date Night Outfit

Statement Sparkle Pants + Festive Blouse

If you’re looking for a dressy winter date night outfit (or perhaps an outfit idea for a holiday party), this is a festive and formal option. Sequin pants are easy to find these days, especially around Christmas/New Year’s Eve and I think they’re a fun piece to have on rotation throughout the winter.

I dressed this outfit up even further with a sparkly, statement-making headband, but you could always go without one if you want a more subtle vibe.

Statement Sparkle Pants + Festive Blouse Winter Date Night Outfit

Sweater Bodysuit + Black Pants

This is my go-to casual winter date night look, and it’s honestly just a good option to wear on repeat throughout all seasons.

I’m a big fan of bodysuits because I think they take the guesswork out of getting ready. Something about it being one main piece that you style the rest of your outfit around just makes things easier in my mind.

I generally wear my bodysuits with a pair of jeans or leather pants, but you could also go with a skirt to switch things up.

Sweater Bodysuit + Black Pants Winter Date Night Outfit

Fur Coat + Blazer + Cowboy Boots + Hat

This look is definitely a big vibe in Aspen, but it would also be cute to wear regardless of where you live. If you have a teddy coat or faux fur coat in your closet, use that as the main focus of your outfit then add a pair of white jeans, a sweater, and a plaid jacket to complete the look.

I have always loved wide-brimmed hats and think they make for a great winter accessory, but I know they aren’t for everyone so you could easily leave that out.

Fur Coat + Blazer + Cowboy Boots + Hat outfit

Sweatsuit + Sherpa Jacket + Sneakers

Just heading out on a quick coffee date? There’s no need to get all dolled up, so opt for a comfy sweatsuit, sherpa jacket, and pair of white sneakers.

I reach for my sherpa jacket constantly throughout the winter months, so I’d highly recommend adding one to your wardrobe if you want to create a variety of cozy yet cute looks. It’s easy to dress this type of jacket up or down depending on where you’re going.

Sherpa Jacket Winter Date Night Outfit

Puffer Vest + Sweater + White Jeans + Winter Accessories

If you’re doing any type of winter activities during your date night, I’d recommend leaning into the more practical outfit options. The last thing you want is to be freezing while you’re trying to enjoy some one-on-one time.

The key to making this kind of outfit look a bit more elevated and “special” is to reach for a vest or puffer jacket that’s a bright color. This gives the outfit a focal point and adds a more styled feel to the overall look.

Puffer Vest and sweater outfit

Denim Jacket + Jeans + Pops of Fur

Similarly to the all-black outfit idea above, it’s fun to go with a denim-on-denim look from time to time. Adding fur boots or a teddy coat offers a way of breaking up the fabric so it doesn’t look too overwhelming.

Denim Jacket and jeans outfit

Blazer + Skinny Jeans + Tall Boots

If I had to take a bet, I’d guess that you already have a pair of skinny jeans, a black blazer, and a pair of tall boots in your closet. These are all closet staples that can be combined to create a sophisticated look for any type of date night.

I like to wear black turtleneck sweaters on winter date nights because they keep you covered (aka cozy and warm) but they also give off an elevated feel. Adding a blazer on top makes things look even more formal, but you could always swap it out for a long cardigan or coat.

Skinny Jeans + Tall Boots outfit

Oversized Sweater + Tall Boots

Another mindless and fool-proof option for date night? An oversized sweater paired with any bottoms of your choice. This might be the comfiest look on the entire list, and I love that you can style this type of sweater with any bottoms and shoes.

Oversized Sweater + Tall Boots outfit

Oversized Blazer + Denim

I recently wore this outfit on a date night with Matt and will definitely be repeating it because it’s sooooo easy to put together yet looks like you put in a lot of effort.

Just start with any basic, long-sleeve t-shirt, layer on a blazer (ideally one that’s oversized), and slip into some jeans. Add ankle booties, knee-high boots, or even heels and you’ll be ready to go. You could also accessorize with gold jewelry or a colorful purse to take things up a notch.

Oversized Blazer + Denim outfit

Strapless Tailored Top + Trousers

While this outfit might only be practical if you live somewhere with mild winter temps, I still wanted to include it because I think it’s really cute. My exact top is sold out, but any strapless and tailored top would emulate the same vibe.

Also, opting for wide-leg trousers rather than a pair of everyday jeans might seem like a small swap, but it can make your outfit look much more special.

Strapless Tailored Top + Trousers outfit

Trench Coat + Matching Skirt Set

Trench coats are such a fun piece to incorporate into your fall, winter, and spring outfits. They’re not only practical but they aren’t something you’d necessarily wear every day, making them the perfect jacket choice for a date night.

Similar to the look above, this outfit might only make sense if you live in California or Florida, but it’s a sexy and feminine option for those of you who have more mild winters!

Trench Coat + Matching Skirt Set Winter Date Night Outfit

Silk Top + Black Pants

There’s something about a silk top just screams date night to me. I love the strapless look of this particular shirt, but you could also wear a long-sleeve silk blouse if you need something with more coverage.

This outfit would look cute with a sherpa coat, leather jacket, or wool trench—the options are basically endless.

Silk Top + Black Pants Winter Date Night Outfit
Which winter date night outfit is your favorite? Let me know in the comment section below!

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