7 Winter Date Night Outfits That are Romantic and Cozy

Please note that this post may contain affiliate links and any sales made through such links will reward us a small commission – at no extra cost for you.

You’ve picked the best winter date idea, so now you need to find stunning winter date night outfits to make the romantic occasion extra special. For your next winter date nights, consider trying on chic and cozy looks.

Think skinny jeans with knee-high boots. A comfy-cozy sweater dress, or slip on a cute skirt and an elegant statement coat to impress your partner. There are many different ways that one can go about creating perfect winter date night outfits, so if you are still trying to put together a date-worthy look – refer to these ideas to help you get dressed up!

Casual Dates

1. Grey coat + Black Sweater + Skinny Jeans + Over-the-knee-boots

Winter date night look book with turtleneck sweater

Because we are now saying hello to the freezing temperatures, the dress code for the winter weather calls for winter date night outfits that are fashionable and functional. Do you need outfit inspiration? A cashmere sweater and an elegant belted coat are great options for your next date.

The classic black sweater creates the best foundation to help you create the best cold-weather ensemble. You can layer on the long coat to give you more warmth and make your look pop. To round off your casual date night look, reach for a pair of jeans in a darker wash. Slip-on black over-the-knee boots and, accessorize with gold hoops to help you get through your special night in style.

Dinner Date

2. Sweater dress + Rib Jacket + Chain crossbody bag + Ankle strap heels

Swap your summery slip dress with chic sweater dresses for the winter season. The long sleeves will keep you warm during the cold weather, while the ruffle hem will give you a sleek look for your next date. And since you will be going on a formal date, throw on some sophisticated black high heels to elevate your look even further. Just layer on a long coat and, you’ve got yourself the perfect date night look.

Hot Cocoa Dates

3. Statement sweater + Shoulder bag + Ankle boots + Leather skirt

Winter date night lookbook with leather skirt

Spend quality time with your significant other in style. Go for a black leather skirt that you can look cute in while you enjoy a good conversation and a warm beverage. And since we are in the cold winter months, it’s the perfect time to try out a statement sweater. The neutral color check print is the right balance between the black faux leather skirt.

To give your date ensemble a stylish feminine touch, slip on Buckled Suede Leather Heeled Boots.

Wine tasting date

4. Turtleneck sweater + Suede skirt + Over the knee boots

Winter date night look book with black over the knee boots

What better way to beat the winter blues than to dress up and go on a wine tasting date? Whether you’re going to your local wine tasting farm or a restaurant, you need to find a cute and cozy outfit.

If thinking of a great winter date night outfit idea is starting to be a difficult task, we have the perfect winter date night outfit to help you get of a style rut.

When in doubt, wear a suede skirt. It’s a great option if you have pants fatigue. And, most importantly, the stretchy fabric will not only hug you in all the right places but will also give you a comfortable fit.

Since this skirt reveals a little bit of skin, team it up with black tights to give you some coverage.

When wine tasting during winter, wearing an oversized sweater is a great way to save you from the chilly air. And it will pair perfectly with your skirt.

To take your stellar outfit to the next level, accessorize with a vegan leather shoulder bag.

Second date

5. Wrap sweater dress + Faux fur jacket + Huggie earrings + Ankle strap heels

Would it be the holiday season without wearing a black sweater dress? It is a cold-weather wardrobe staple that is immune to fashion trends. The jet-black hue will complement your accessories and make you look luxurious.

To pull off a black dress during the winter, opt for a maxi length. You can’t go wrong with a black sweater dress, especially for a romantic date out. And this elegant wrap dress will be the perfect pick for a candle-lit dinner.

The V-neck adds a little sexy touch to your look, while the waist tie will give you a gorgeous silhouette. If creating monochromatic outfits is part of your personal style, match your white dress with a faux fur jacket.

This particular jacket is an absolute show-stopper and will get you so many compliments.

To finish your look, Pair your dinner date-appropriate dress with nude ankle strap heels, white jewel-adorned huggie earrings – and you’ve got yourself one of the best winter date night outfits.

Related post: Best Place To Buy Earrings Online To Elevate Your Look

Museum date

6. Turtleneck sweater + Moto jacket + Chain crossbody bag + Skinny jeans + Pumps

Winter date night look book with moto jacket

Keep the spark alive by dressing up in a cool yet classy outfit for your upcoming winter museum date.

Blue jeans are a winter must-have. They are versatile enough to pair well with a turtleneck sweater to create the perfect winter date night outfit.

To take your look up a notch, throw on a biker jacket. Nothing gives off a cool woman vibe than a moto jacket. And since you will be admiring art in a fancy museum, swap your go-to flats for some luxe nude pumps. The 3 1/4 heel will provide some ease and comfort than sky-high 6 inch heels.

As for the accessories, keep it chic with a crossbody bag from Madewell. It is lightweight, so you don’t have to worry about it straining your shoulder. It also has enough space to hold your museum tickets.

Theater date

7. Turtleneck sweater + Burgundy coat + Shoulder bag + Pumps

Winter date night look book with red pumps

This winter date night outfit is the perfect balance between business chic and romantic. It is sophisticated enough to be worn from the office to date night.

The burgundy coat will not only go well with a bold red lip, but it will also keep you warm on cold days. Team it with a pair of straight-leg jeans and a pair of red pumps that exude effortless elegance. This look wouldn’t be complete without a timeless shoulder bag to round off your date night look.

Finding winter date night outfits that will give you a boost of confidence is not an easy task. However, with these seven best date night outfit ideas, you will look fabulous no matter what your date night plans are.

Christmas is just around the corner and, that can only mean one thing: It’s time to look for the best Christmas dinner outfits.

Up next: What to Wear to Christmas Dinner to be Classy yet Comfortable

Winter date night outfit ideas
Temwa Namandwa
Hi! My name is Temwa and I have an obsession with all things lifestyle. Whether it's home decor, classy fashion, beauty products, or gift ideas -- you will find me writing about those topics. When I'm not sitting at my laptop, you will find me making press-on nails over the weekend!