Date nights are important to schedule throughout the year with your significant other – even on the coldest of days. Though venturing out into the cold isn’t always the funnest, having uninterrupted alone time as a couple is always a good idea. Today, I’m rounding up 10+ winter date night outfits for your next adventure. You don’t have to sacrifice style just because of the cold weather.

10+ Winter Date Night Outfits

Winter date night outfits can sometimes be tricky because you don’t want to be cold, yet you want to feel fashionable and comfortable. The good news is you can have all of the above with these outfits below.

Before putting together your date night outfit in the winter months, you want to think about what you’ll be doing for your date.

Are you:

  • Going to dinner
  • Seeing a movie
  • Headed to the theater to see a musical/play
  • Ice skating
  • Going to a concert

Then you can decide what would be most appropriate to wear for the setting and the weather. Below, I have a good mix of casual winter date outfits, some for cold weather, cute winter date night outfits and sexy winter date night outfits. Each outfit has affiliate links below, so you can easily shop each look.

Mini Skirt Paired with a Sweater

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The first two outfits incorporate a mini skirt into the look. These sexy winter date night outfits are stylish, yet comfortable, and are the perfect looks to wear to dinner or to the theater.

The first look features a tweed skirt with pearl buttons down the front. The second look is a faux leather skirt, and I paired it with a chunky turtleneck sweater. Both are perfect winter date outfits to wear for those dressier occasions.

vegan leather pleated mini skirt, winter date night outfits
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This winter date outfit styles a pleated faux leather mini skirt. If it’s extra chilly that evening, wear tights with the skirt and knee-high boots. Don’t forget your outerwear to stay extra warm. A wool or wool-blend long coat would make the perfect finishing touch. The addition of the beret gives this outfit idea a pop of color and levels up the look.

Sweater Dress Styled with Knee-High Boots

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These might be the only three black pieces I shared throughout December and January. But you all loved them, so I wanted to be sure to include in this roundup. A black sweater dress is timeless and a great option for those times when you’re needing dressy winter date night outfits. Both of these are from Walmart, and paired them with knee-high boots to give the legs extra coverage.

If you want to give the look a more edgy vibe, try layering a black leather jacket over the dress. This look is perfect to wear for a dinner date or to a musical/play.

black mini sweater dress with over-the-knee boots, winter date night outfits
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This black sweater dress is a mini dress with a pleated skirt. It’s from Amazon and comes in several colors besides the black. I chose to wear over-the-knee black boots, so my legs would be mostly covered by the boot. I also have black tights on to give the extra coverage and warmth.

These pearl headbands are a great way to jazz up a look without having to wear a hat. They come in a three pack and love the pearl embellishments.

cream sweater dress with brown boots
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If you prefer lighter tones to wear, I love this midi sweater dress. I’m wearing my trusty Spanx undergarment to give a more smoothing look. To add texture and color, layer a scarf around your neck or pair a suede moto jacket with the dress. I like to wear knee-high boots with most midi dresses in the winter. If you don’t love wearing tights, it’s a great way to cover the legs.

Outerwear Layered Over a Skirt and Leggings

pleated mini skirt with wool coat, winter date night outfits
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These next few looks incorporate outerwear into the outfit idea. This outfit above is styled with a pleated mini skirt and a fitted turtleneck. Then, I layered a wool coat over the top to keep me extra warm and toasty.

Throughout the winter, if you’re wearing a dressy outfit, I always recommend a wool or wool-blend coat. It’s a great winter basic to wear throughout the season. HERE I rounded up my favorite camel coats.

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These next two looks are two other cold weather winter date night outfits, but they’re more casual compared to the first. The base layer for both outfits are faux leather leggings with a basic white bodysuit with long sleeves. Two great staples to have to create a variety of outfits.

If you’re doing something more active like ice skating, the first outfit above is a great option to wear. I recommend adding gloves and beanie too, if you’re going ice skating.

The second look features a puffer vest. This would be a fun look to wear to a brewery during the day or going to a sporting event (that’s indoors). It’s laid back and casual, but a little fun and spicy with the leather leggings and knee-high boots.

Flare Jeans and Leggings Styled with a Turtleneck

flare jeans with white bodysuit
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These next two outfits are casual winter date night outfits. The above look features flare denim pants with a fitted turtleneck. This would be perfect to wear on a first date. It’s cute and casual, yet a little elevated with the pumps. You can also pair with a pointed toe bootie that gives the same look, but a little warmer than a pump.

Another option to wear in place of the flare jeans are faux leather pants like THESE. You can wear pumps with them or a covered heel bootie like THESE.

black leggings with tunic-style sweater
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This tunic-style sweater is one of my favorite sweaters from Amazon. It’s a Free People look-alike, and actually prefer this one over the Free People option. You can pair this with faux leather leggings or with skinny jeans – whatever you prefer. Then, I finished the look with knee-high boots. Don’t be afraid to mix brown boots with black pants. 🙂

Mini Sweater Dresses with Knee-High Boots

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The final two looks in this winter date night outfit roundup are these two mini sweater dresses. They’re a little casual, yet elevated, and definitely great examples of cute winter date night outfits.

I love the look of the Western-inspired boots paired with the sweater dress in the first outfit. You can even add a wool hat.

See what a simple scarf can do to an outfit in the second photo? It gives it that added layer that creates a luxe look with little effort. A sweater dress with a knee-high boot is honestly a great option for a variety of date night activities from dinner to a movie and a play. Wear over-the-knee boots or add tights to make it even more winter-weather appropriate.

Which look would you most likely wear on your next date night during cold weather? Let me know in the comments below!

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