50+ Stylish Winter Date Night Outfits (2024)

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I have rounded up 50+ ideas for winter date night outfits. Whether you are looking for a very cute winter date night outfit, a casual winter date outfit, or a fancy, winter dinner date outfit, you’ll find the perfect date night outfit with lots of options included below. 

I included lots of classic winter date night outfit ideas like a leather jacket, little black dress, and knit dresses (one of my favs!). I’ll keep this blog post updated with perfect winter date night outfits.

Pin this post so you can come back for winter outfit inspiration. There are already beautiful pieces online for this winter season and I am excited for what is to come!

Whether you are looking for a cute winter date night outfit, casual winter date outfit, or a fancy winter dinner date outfit, you’ll find the perfect date night outfit here.

Some of the below winter date outfits will be perfect for a casual winter date, such as a coffee date or cozy afternoon lunch. Other outfits will be perfect if you are looking for fancy winter date night outfits for a special occasion or an exciting first date. 

Whatever your personal style this winter, know that there are no hard and fast rules when it comes to dressing for winter date nights. The most important thing is that you feel comfortable and enjoy yourself. Incorporate your personal style and have fun dressing this winter.

Winter Date Night Outfits:

Whether you are looking for a cute winter date night outfit, casual winter date outfit, or a fancy winter dinner date outfit, you’ll find the perfect date night outfit here.

Without further ado, here are some of my favorite pieces you can mix and match for the perfect winter date night outfits. Hope you get lots of inspo from these cute winter outfits for date night.

Winter Date Night Outfit Idea: Leather Jacket

One of the perfect date night outfit pieces is a quality leather jacket or moto jacket. A leather jacket is so versatile and a statement piece for your wardrobe, whether for a date night outfit or day-to-day outfits.

Whether you are looking for a cute winter date night outfit, casual winter date outfit, or a fancy winter dinner date outfit, you’ll find the perfect date night outfit here.

Adding a leather jacket with a little black dress or some skinny jeans makes easy date outfits. Leather jackets work for casual date outfits, dinner date outfits, and most date night adventures. I’ve rounded up some cute leather jacket and moto jacket options below.

Winter Date Night Outfit Idea: Little Black Dress

One of my favorite winter date night outfit ideas is a little black dress. Little black dresses never go out of style and are one of the best investment pieces for fancy date night outfits.

It’s really easy to personalize a little black dress by mixing and matching it with some cute accessories below (see some of my favorite picks at the end of this blog post!)

I have rounded up 50+ ideas for winter date night outfits. Whether you are looking for a very cute winter date night outfit, a casual winter date outfit, or a fancy, winter dinner date outfit, you’ll find the perfect date night outfit with lots of options included below.

The best thing about an elegant little black dress is that you can wear it for a special occasion to a nice dinner date or you can tone it down by pairing it with a leather jacket or a moto jacket.

With little effort, you can completely change the look of a little black dress with different accessories. Find your perfect winter date night dress below. I love buying pieces that will work year-round.

Winter Date Night Outfit Idea: Date Night Dresses

Along with little black dresses, other cute dresses make the perfect date night outfits. I love dresses for winter date nights as they are one piece, which makes the whole outfit.

They are really elegant and simple to accessorize for a complete look.  There are so many pretty dresses out right now for winter date nights. I have picked a few of my favorites. I love the winter colors!

Winter Date Night Outfit Idea: Skinny Jeans

Skinny jeans are another key item to have in your wardrobe. There are so many styles, colors and finishes of skinny jeans that you can have as staple investments.

A classic pair of skinny black jeans or a darker wash are great options for winter date night outfits. Having a classic (and comfortable) pair of skinny jeans that suit your personal style is a great way to mix and match with cute tops for date night.

There are so many cute winter date night outfits with jeans once you have the perfect pair of skinny jeans. Here are some of my favorite styles that feel great on. 

Winter Date Night Outfit Idea: Tops with Shoulder Detail

Tops with shoulder detail paired with skinny jeans are very cute winter outfits for date night. These tops in the prettiest colors and styles for winter. In the cooler months, it’s an easy way to show a little skin without freezing! This can turn a more casual date night look into a fancier date night outfit.

These tops come in various shapes and styles so you can find the perfect one for your body shape. As I mentioned above, the most important thing about your winter date night outfit is that you feel comfortable and confident in your outfit.  We all have different ideas of what a cute outfit for a winter date night means so pick and choose what suits you best. 

Here are some pretty tops with shoulder detail that I love right now.

Winter Date Night Outfit Idea: Oversized Blazer

Oversized blazers make another great date outfit for winter, especially in the cooler months. Oversized blazers can be dressed up or down for winter date-night outfits or dinner date outfits.

One of my favorite things about oversized blazers is that you can really incorporate your personal style with blazers. They can be elegant and chic or more chic and grunge. 

Here are some cute oversized blazers that you can use to elevate your date night outfits.

Winter Date Night Outfit Idea: White Shirts & Blouses for Classic Versatility

Whether you are looking for a cute winter date night outfit, casual winter date outfit, or a fancy winter dinner date outfit, you’ll find the perfect date night outfit here.

The classic white shirt & blouse transcends time and trends. It’s a staple that effortlessly balances sophistication and simplicity. A quality white shirt and blouse will carry you throughout all seasons and is the perfect addition to your capsule wardrobe for winter date outfits.

Winter Date Night Outfit Idea: Luxurious Leather That Gives a Touch of Edginess

Leather pants have been all the rage over the past couple of years. Leather pants are the perfect alternative to skinny jeans. Having a good pair of leather pants is a staple in your wardrobe, especially during winter. 

Whether you are looking for a cute winter date night outfit, casual winter date outfit, or a fancy winter dinner date outfit, you’ll find the perfect date night outfit here.

Spanx has a particularly great variety of comfy leather pants. Spanx is known for being super comfy and fashionable. 

This season, it’s all about incorporating leather into unexpected pieces, such as dresses and skirts, to create a modern and edgy look. Leather leggings are still the perfect way to dress up a white shirt. Add chic accessories to elevate your date night look.

Winter Date Night Outfit Idea: Patterned Tights

Tights have a long history of accessorizing and adding a touch of flair to outfits. This season, they become a canvas for artistic expression and the perfect way to add some warmth to your winter date night outfit.

Winter Date Night Outfit Idea: Darker Winter Florals

Floral patterns have been popular since the Victorian era. For Fall/Winter 2024, they take on a darker, more dramatic tone, inspired by the romanticism of the 19th century.

Whether you are looking for a cute winter date night outfit, casual winter date outfit, or a fancy winter dinner date outfit, you’ll find the perfect date night outfit here.

Winter florals are wardrobe staples that are perfect for winter date nights. Here are some options that make the perfect chic winter date outfit.

Winter Date Night Outfit Idea: Ultra Warm Coats with Faux Fur Accents

Living in San Francisco has taught me the importance of a beautiful long coat. Having a few good long coats in your wardrobe will be the perfect investment for winter date nights that will carry you into winter. 

I have rounded up 50+ ideas for winter date night outfits. Whether you are looking for a very cute winter date night outfit, a casual winter date outfit, or a fancy, winter dinner date outfit, you’ll find the perfect date night outfit with lots of options included below.

Long coats can be an outfit in themselves if you are going to be outdoors on your date. Faux fur coats are the perfect accompaniment to the little black dress or skinny jeans mentioned above. These coats make the perfect date night outfit, especially for winter date night outfits.

There are so many beautiful coats available to suit all body types. Some of my favorite retailers for classic long coats are River Island, Karen Millen, Ann Taylor and Express. They always have classic coats with pretty details that make the coats memorable.

Winter Date Night Outfit Idea: Tailored Outfits that are Effortlessly Chic

For a perfect winter date night outfit, a tailored look can take you from day to night. Tailoring has evolved to become a symbol of sophistication and confidence. This season, it takes a gender-neutral approach, offering chic and comfortable options for all.

Ann Taylor, Karen Millen, Express and River Island all do really pretty tailored pieces. Tailored dresses are always an effortless look that look really chic and put together.

Winter Date Night Outfit Idea: Knit Dress and Sweater Dresses

For winter date night outfits, knit dresses, and sweater dresses are great options. They can be perfect for casual date night outfits or a dinner date outfit depending on the fit and style. Sweater dresses are classic winter pieces and great capsule pieces that will last you through the season.

How you accessorize knit dresses is key for dates. Adding a cute gold chain belt, pretty headband or statement necklace can make all the difference. See lots of my favorite accessory picks below.

Using accessories to add touches of your personal style is a great way to lift the outfit and bring sweater dresses to life. You don’t always need a new outfit for every date. You can change up looks by mixing and matching accessories. With a little effort, sweater dresses can look fun.

Here are some pretty knit dresses and sweater dresses for the perfect date outfit.

Winter Date Night Outfit Idea: Comfy, yet stylish boots

Whether you are looking for a cute winter date night outfit, casual winter date outfit, or a fancy winter dinner date outfit, you’ll find the perfect date night outfit here.

I  still love a pair of (comfortable) boots so I can dress up throughout winter. I love Sarah Flint boots as they are so comfortable and last for years. You can read my full Sarah Flint boots review here. My Sarah Flint code SARAHFLINT-CCLORNA1 gets 15% off your first pair of Sarah Flint shoes.

Winter Date Night Outfit Idea: Comfortable shoes

I think 2020 & 2021 taught us the luxury of being comfy! I found Birdies shoes in 2019 and am now in love with the brand. They are like slippers, but very pretty slippers that you can wear around the house or on dates.

Whether you are looking for a cute winter date night outfit, casual winter date outfit, or a fancy winter dinner date outfit, you’ll find the perfect date night outfit here.

Birdies has shoes that are perfect for work, dates, fancy nights out or for lounging around the house. I have picked out some fun options for pairing with skinny jeans for a casual date outfit. I have also picked cute ones for a dinner date outfit. Birdies are such comfortable shoes that I highly recommend.

Read my full Birdies Review and see all of my favorites here.

Get $30 off with my Birdies coupon code. All you need to do is click through this link to be directed to the Birdies site with my Birdies discount code already applied to your first order.

Winter Date Night Outfit Idea: Pair of Heels

I love a pair of (comfortable) heels so I can dress up for a special date night. I love Sarah Flint heels as they are so comfortable and last ages. You can read my full Sarah Flint review here. My Sarah Flint code SARAHFLINT-CCLORNA1 gets 15% off your first pair of Sarah Flint shoes.

Sarah Flint shoes are expensive but they are truly worth it! I have 4 pairs and love them all so much.

Winter Date Night Outfit Idea: Hairband

It’s time to talk about some fun accessories for your stylish winter outfits. I love accessorizing. It fills me with so much joy. There is nothing like a good headband to add instant glam. 

I have rounded up 50+ ideas for winter date night outfits. Whether you are looking for a very cute winter date night outfit, a casual winter date outfit, or a fancy, winter dinner date outfit, you’ll find the perfect date night outfit with lots of options included below.

I have picked out some beautiful headbands that can be worn to glam up a casual winter date night outfit or add the finishing touches to a fancy winter date night outfit. Date outfits are your time to get creative and use all your extra sparkly items! Headbands are an easy way to turn a cute date night outfit with jeans into a fun statement.

Winter Date Night Outfit Idea: Pretty bag

I love dainty, pretty bags and bring them out at the weekend for date nights. During the week, I appear to need the kitchen sink in my bag so I always tend to have a bigger bag with me. These are some pretty winter date night purses for carrying all of your important things while adding a touch of glam.

I have rounded up 50+ ideas for winter date night outfits. Whether you are looking for a very cute winter date night outfit, a casual winter date outfit, or a fancy, winter dinner date outfit, you’ll find the perfect date night outfit with lots of options included below.

Winter Date Night Outfit Idea: Jewelry

I have included lots of simple accessories below for adding some glam to your winter wardrobe.

Your casual winter date night outfit can get a twist of glam with a dainty gold necklace, some studs or even a statement necklace. There are so many accessories that you can use to give you easy winter date night outfit ideas that suit your personal style.

I have rounded up 50+ ideas for winter date night outfits. Whether you are looking for a very cute winter date night outfit, a casual winter date outfit, or a fancy, winter dinner date outfit, you’ll find the perfect date night outfit with lots of options included below.

Accessories and jewelry are a great way to mix things up and create new looks from what you already have in your wardrobe. 

Here are some cute jewelry pieces to upgrade your date night looks.

Hope you enjoyed browsing through my top ideas for winter date night outfits. As I mentioned above, I’ll keep this blog post updated for lots of new options for winter date night outfits. Pin this blog post so you can come back at any time to get some new ideas for cute outfits for winter.

Whether you are leaning towards a little black dress or a leather jacket and jeans for your perfect date night outfit, you will look equally fabulous. Enjoy your date night!

Whether you are looking for a cute winter date night outfit, casual winter date outfit, or a fancy winter dinner date outfit, you’ll find the perfect date night outfit here.

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About Lorna Ryan

Lorna's fashion & beauty journey began on runways, including NYFW, which sparked her love for all things chic. Lorna spent two years as a SephoraSquad ambassador, sharing hero beauty products. Lorna unveils coveted beauty gems, the latest fashion trends, and best-kept jetsetter escapes.

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