Despite having been married for a while now, Mitch and I still make a point to date each other. I think regular date nights are important, even when the temperatures have dropped below freezing and snow is piled ridiculously high around us. Why? Because dates are a great way to nurture your relationship, get to know your partner even better, and spend quality time together. Quality time alone together. 

Admittedly, I also love date nights because they give me the opportunity to dress up. I don’t have to worry about whether the outfit I’m wearing is OK for running all around town with my kids. I can simply look and feel beautiful. 

To give you some inspiration, I’m sharing a roundup of date night outfit ideas that will keep you warm and comfortable,as well as super stylish during winter. (P.S if you’re in need of some Chicago winter date ideas, I’ve got you covered there too!)

7 Date Night Outfit Ideas in Winter

Sweater Dress, Wool Wrap Coat, Riding Boots, Crossbody Bag

Sweater dress, topcoat, boots, handbag, earrings, and bracelet

Turtleneck Sweater Dress (Sold out but similar HERE) / Wool Wrap Coat (Sold out but similar HERE) / Leather Riding Boots / Crossbody Bag / Pearl Earrings / Hinge Bracelet

Sweater dresses are among my favorite things to wear in the winter because they’re cute but still surprisingly warm. For this look, I styled a turtleneck sweater dress with leather riding boots. It’s perfectly preppy and I love this look as a first date/winter date night outfit! To complete the outfit, I added a crossbody bag, pearl earrings, and my favorite hinge bracelet.

Black Suede Dress, Black Tights, Brown Knee High Boots

black winter date night outfit idea

Black Suede Dress (Sold out but similar HERE) / Black Tights / Bristol Knee High Boots

I adore this look for a cold weather winter date night outfit. I had a ton of requests for the black suede dress with brown knee high boots, and when I styled them together I was a little surprised by just how much I loved this look. To make it appropriate for those super cold Chicago nights, I added a pair of black tights. I think it definitely takes this look from a fall fav to an essential outfit in the winter months.

Cashmere Crewneck Sweater, Cropped Jeans, Topcoat, Ankle Boots, Stud Earrings, Leather Crossbody Bag

winter date outfit with jeans

Cashmere Crewneck Sweater / Cropped Demi-Boot Jeans / Ivory Topcoat (Sold out but similar HERE) / Ankle Boots / Stud Earrings / Black Leather Crossbody Bag

If you’re looking for casual date night outfit ideas for winter, check out this one! I LOVE my cropped demi-boot jeans, but you can easily swap them for your favorite pair of skinny jeans. I styled them with a gorgeous cashmere crewneck sweater and ivory topcoat. Then, to complete the look, I added ankle boots, stud earrings, and a black leather crossbody bag.

Cable Knit Sweater, Faux Leather Skirt, Wool Parka, Ankle Boots, Crossbody Bag 

cute winter date outfit

Cream Cable Knit Sweater / Black Faux Leather Skirt / Black Wool Parka / Black Leather Crossbody Bag / Black Ankle Boots 

This is one of my favorite cute winter date night outfits. It’s a stunning winter outfit with a fun twist thanks to the faux leather skirt. I paired it with a cream cable knit sweater, then added a black wool parka because you’re going to need some added warmth as you make your way to and from your date. I love the way the skirt looks with ankle boots, so I added those, as well as a black leather crossbody bag.

Turtleneck Sweater, Demi-Boot Jeans, Wool Wrap Coat, Leather Boots, Leather Tote Bag 

winter dinner outfit

Tan Turtleneck Sweater / Demi-Boot Jeans (Sold out but similar HERE) / Wool Wrap Coat (Sold out but similar HERE) / Leather Ankle Boots / Leather Tote Bag

Here’s one of my go-to winter date night outfits with jeans. I styled the tan turtleneck and jeans with a wool wrap coat, but you could totally swap the coat for a leather jacket. Either one would look fantastic with leather ankle boots and a leather tote bag.

Velvet Dress, Black Knee-High Boots, Fleece Lined Leggings

Black Velvet Dress in winter

Black Velvet Open-Back Dress / Black Knee-High Boots (Sold out but similar HERE) / Fleece Lined Fake Opaque Tight Leggings

When putting together dressy winter date night outfits, this is one of my favorite styles. The Velvet Open-Back Dress from Banana Republic is my favorite warm little black dress. I styled it with black knee-high boots. Then, for added warmth, I added fleece lined leggings. But here’s the thing… these aren’t your average leggings. They make it look like you’re wearing opaque tights so no one will ever know you’re actually wearing super warm leggings. Love it!

Cable-Knit Cardigan Sweater, Pleated Midi Skirt, Belted Wool Wrap Coat, Clutch, Pearl Earrings, Slingback Pumps

pleated midi skirt winter outfit

Cable-Knit Cardigan Sweater (Sold out but similar HERE) / Pleated Pull On Midi Skirt / Belted Faux Fur Collar Wool Wrap Coat (Sold out but similar HERE) / Velvet Convertible Clutch (Sold out but similar HERE) / Pearl Stud Earrings (Sold out but similar HERE) / Slingback Pumps (Sold out but similar HERE)

There are so many options for classy winter date night outfits, but it’s hard to top this one. You can’t go wrong with a classic black and white outfit. The cable-knit cardigan goes perfectly with this pleated pull on midi skirt. I like to throw on my belted wool wrap coat for the commute because it’s so chic and SO warm. Then, to finish this look, I added one of my go-to evening clutches, pearl earrings, and slingback pumps. 

Which outfit can you see yourself in on your next date night?

I’d love to hear which outfit caught your eye. If not, maybe there were a few pieces you would love to add to your wardrobe. Regardless, I want to hear from you! Feel free to share your thoughts, tips, ideas, and suggestions!

For more outfit inspiration, style tips, and some of my favorite fashion finds, check out the blog.