The Top 10 Best Winter Date Outfits to Keep You Warm and Stylish

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You’ve planned the perfect winter date night. The two of you are going to get cozy in front of the fireplace, sip hot cocoa, and watch your favorite holiday movie on Netflix… so what’s missing? You! It’s important to dress comfortably but fashionably on your winter date night, or else you could be chilly and uncomfortable throughout your evening. Luckily, many stylish outfit combinations will allow you to have fun with your significant other without sacrificing your comfort. Here are our top 10 best winter date outfits to keep you warm and stylish!

The best clothing for dates in the winter

A long-sleeve turtleneck sweater

A long-sleeve turtleneck sweater

These are great for layering, and if you want to dress them up with a blazer or oversized cardigan, they can be dressed up easily.

Booties or Chelsea boots

date night outfit winter

You’ll look chic in these versatile shoes that go with anything from jeans to dresses.

Fur vest or jacket

winter date outfit

 If you’re looking for an extra layer of warmth this winter, a fur vest is a way to go!

1) Skinny Jeans & a Flannel Shirt

cute winter date outfits

A great winter date outfit is something you’ll want to wear in both the winter months and when it gets colder outside. The best outfits are ones that can be dressed up or down, depending on the occasion. A cozy pair of skinny jeans paired with a flannel shirt will keep you warm while still looking cute, chic, and stylish.

Also, Read Top 10 casual winter outfits that are both comfortable and stylish

2) A Pair of Dressy Boots with Black Leggings

first date outfit winter

A great date outfit is all about what makes you feel confident and beautiful. A stylish winter date outfit is a little more complicated than a summer one since it’s so much colder outside. Still, if you can think of a good idea for an activity that doesn’t involve being in the elements too much, then wearing your favorite dressy boots with black leggings should do the trick!

3) Patterned Cardigan & a Jumper Dress

winter date night outfit dress

A cardigan is a perfect way to look chic while staying warm, while a jumper dress will keep you looking cute without getting too cold. An oversized sweater is great for adding warmth but pair it with skinny jeans or leggings for a more stylish option. Pile on some accessories (a pom-pom scarf, furry hat, gloves) for a little extra winter flair. Don’t forget boots!

4) A Pair of Jeans with a Vest

dinner date outfit winter

This outfit is perfect for winter dates because you will be able to stay warm while still looking cute. The best part of this outfit is that it doesn’t require you to dress too warmly. Plus, the jeans can be worn throughout the year because they can be layered with vests, sweaters, t-shirts, etc.

5) A Leather Jacket over a Chic Long Sleeve Top

winter date night outfits

A warm leather jacket is a perfect addition to a winter date outfit, as it will keep you warm while looking stylish. Plus, you’ll be able to change your outerwear with the weather; all while keeping your look fresh! Here are our top picks for the best leather jackets for winter.

1) The Minkoff Leather Jacket in Black – $228 This jacket is made of 100% lamb leather and features a ribbed collar for added detail.

Also, Read Top 15 best Baddie winter outfits to wear

6) An Ombre Sweater & Biker Shorts

cute winter outfits for date

This outfit is anything but boring. With the biker shorts, we’re keeping it casual but adding a fashion-forward touch. To add some flair, we recommend an ombre sweater in a neutral color like brown or grey. That way it’s not too dark for winter. If you want to go all out with this look, try tying your hair back into a ponytail with a bright red headband and matching lipstick.

7) A Puffer Jacket over an Asymmetric Skirt

date outfits for winter

Puffer jackets are the best way to stay warm in the winter. The puffer jacket is also a great layering piece because it can be worn on its own or with other layers, like an asymmetric skirt.

A puffer jacket over an asymmetric skirt is a perfect date night outfit that will keep you both warm and stylish!

8) Super Cool Overalls over a Band Tee

winter date night outfits 2022

Super cool overalls are a fun way to dress up your winter date outfit. This can be paired with anything from a band tee, turtleneck, or sweater. It’s the perfect casual look that will keep you warm while keeping you stylish. Rock this look with some combat boots for an edgier look or some lace-up flats for something more feminine.

9) Pretty Pumps & a Light Cardigan

date night outfit ideas winter

A pretty pump is a winter essential. Plus, you can always layer a light cardigan over it in case of an evening chill. Layer on a faux fur coat for even more warmth. Add a wool hat, scarf, gloves, and booties for the complete look.

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