Winter Date Night Outfits

If you want your winter date night outfits to be on point, this post is for you. We listed 10 great winter date night outfits down below.

If you’re a gentleman, opt for looks with leather jackets, casual sweaters, jeans and a high-quality pair of Chelsea Boots. For the elegant woman, now is the time for leather skirts, leather jackets, flared jeans and formal trench coats. 

In this guide, you’ll find a list of 10 winter date night outfits for men and for women. The list is packed with links, so you can see examples of how they might look. 

10 Winter Date Night Outfits For Guys

Below, you’ll find a list of 10 date night outfits for men. These outfits will help you come across as a sophisticated gentleman who understands fashion, and knows how to dress for his dream woman. 

Turtleneck Sweater with Puffer Jacket

Two staples of your winter wardrobe, which look great with color on in monochrome. How about this navy turtleneck with a classic green puffer

Checked Blazer With White Tee and Jeans

Checks will be in Winter 2021 and beyond. Take a look at how good this black and maroon blazer looks with a plain white t-shirt and jeans.  

Blazer Jacket with Jeans

A casual but classy date night outfit for all occasions, whether it is Saturday nights at a cocktail bar or a five-star restaurant or Sunday mornings walking in the park. A blazer jacket like this will always make you look great  

Textured Trousers and Suede Bomber

Pair textured trousers with a suede bomber jacket for that half-formal half-casual vibe. A simple button-down shirt will complete the outfit. This is a great modern outfit to show your girl that you’re making an effort without overdoing it.   

Denim Shirts, White T-shirt and Dark-Washed Jeans

Denim shirts have been in for a long while now, but they remain a classic winter date night outfit. Pair with your dark wash jeans and Chelsea boots for that casual and comfortable vibe.

A Well-Fitted Dress Shirt and Jeans

A high-quality one-tone dress shirt and reliable pair of jeans will always serve you well. Yes, it’s cold in winter, so add a bold sweater or a trench coat for some extra warmth. Add a pair of good Chelsea boots to complete the look. Some looks never go out of style for men and this is one of them.

Wool Blazer Paired with Dress Pants 

Another formal and refined look that will never go out of style. How about a wool blazer and dress pants and well-polished dress shoes? Grays, navys, whites and blacks will never go out of style with this look. 

Bright and Bold Puffer Jackets 

Bright puffer jackets are making a comeback this fall. Pair them with white jeans for that bright and bold look for those dark and cold winter evenings.  

Tonal Sport Coat

Tonal sport coats are going to be huge this winter. Many high-end brands are doing big things with patterned sport coats. Go for a dash of color to show off your personality.  

Graphic Sweaters

Graphic sweaters are also going to be big in 2021 and beyond. Layer yours with an oversized jacket to keep you and your date warm on those cold winter evenings.  

10 Fall Date Night Outfits For Women

Classy, sexy and warm? How can it be done? These 8 winter date night outfits for women will help you make it happen. 

Sheer Blouse & Leather Pants

What a sexy combination!. The elegance of a sheer blouse with the badass vibes of leather pants. That will warm up any cold weather night for you and your date!  

Blazer Dress & Over-The-Knee Boots

You want to create those boss bitch vibes, with a touch of sexuality? This is the combo for you. How about this white longline dress jacket with black boots?  

Little Black Dress

The little black dress will always be a classy date night outfit whether it’s spring, summer, autumn or winter? Better yet, it can work well on any type of date. 

Floral Jumpsuit

Bright colors work well into winter too. In fact, they might be more needed to brighten up these grey and dreary evenings! How about this figure-hugging floral dress that could look incredible paired with your favorite jewelry.  

Trench Coat and Mini-Dress Combo

A trench coat and mini-dress combo is the sophisticated outfit for this winter and beyond. Pair them with your favorite pointed pumps to be warm, comfortable and incredibly classy. 

Leather Skirt

Leather skirts are going to make a big impact this winter. Pair them with a sweater, tights and boots for a look that’ll turn heads on a cold day. 

A Dark Dress And Heels 

Go for darker shades of blue and green for those cozy coffee dates or cocktails at the bar. Pair them with your most eye-catching heels for a great contrast! 

Add flared jeans to make a statement 

Flared jeans are making a comeback for this winter and beyond. You can pair these with a simple top and shoes and still make an impact on the people you encounter. 

Shirt and Fringed skirt

That classic log-cabin babe style. But, let’s be honest. It looks great no matter what the occasion is. A plaid button-up shirt and a stylish fringed skirt will never serve you wrong. 

Monochrome Leather Jacket

A simple white dress with a black leather jacket is another timeless classic. You’ll look like a badass winter chick every single time. The monochrome look works well on all body types. Your reliable choice for those spontaneous dates. 

Final Thoughts

Your outfit might not make or break your first winter date, but when you look great, you feel great. 

Perhaps that mindset might convince you to invest in one of these outfits now.