25 Winter Date Night Outfits To Copy Right Now


Wondering what to wear on a winter date? Well, I think we all can agree that trying to look cute or sexy in below freezing temps is no easy task. The amount of layers we need just to keep from freezing can leave our winter date outfit looking and feeling frumpy, not to mention your shoe choice is probably the most important decision of the night (no pair of shoes looks good with numb toes.) If you’ve got yourself a winter date coming up, get ready to tackle the cold weather while looking your absolute best. To help you out, here are 25 winter date night outfits to draw inspiration from! Just remember to keep the weather and what activity you’re doing in mind, and you’ll be all set! Good luck!

1. Show A Little Shoulder

Sexy but sweet, the ultimate go-to for a casual dinner date or trip to the movies.

Off the shoulder tops are so cute for winter date night outfits!

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2. Top Off Your Look With A Cute Plaid Coat

Let’s be real, these plaid overcoats are too good to be true. Super warm and totally adorable? It’s a win-win. Toss this coat on over a cute top for an awesome winter outfit to wear on your next date.

Plaid coats are perfect for winter date night outfits!

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3. A Good Flannel Is All You Need

Flannel frenzy, because who doesn’t love a good flannel? This top is a go-to must for casual chic style. You can pair it will leggings and boots for a comfy but put together look, or some jeans and heels for a dressier vibe!

Flannels are so cute and comfy for winter date night outfits!

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Kumer Women's Plaid Shirt Loose Long Sleeve Casual Long Button Down Shirt Top Blouse  

4. Rock A Pair Of Over-The-Knee Boots

These boots can instantly transform anyone into a long-legged goddess. Pair these boots with a cute skirt and sweater, a dress or jeans! They literally look good with everything and will keep those bare legs warm! A great addition for dressing up those winter date night outfits!

Over the knee boots are perfect for winter date night outfits!  Over the knee boots are perfect for winter date night outfits!

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  JollyChic Women's Candy Color Cashmere Wool Thicken Winter Coat (8, White)

5. Layer Up

Layer up your winter favorites for a comfy cute look. An outfit must for those beautiful chilly days. Layer a warm pea coat or wool coat over a denim jacket for ultimate winter street style.

Layering up is a great idea for winter date night outfits!  Layering up is a great idea for winter date night outfits!

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6. Suede Skirt

Savvy in suede, these adorable skirts add just the right texture for a cozy yet dolled up look. Just the right balance between dressy and casual for your next date!

Suede skirts are perfect for winter date night outfits!  Suede skirts are perfect for winter date night outfits!

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7. Flirty & Feminine

Pair a comfy sweater and a sleek little skirt and you’ve got yourself an adorable flirty date night look. Perfect for Valentine’s day or a romantic dinner!

Sweater and skirts are perfect for winter date night outfits!

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  Women Turtleneck Long Bell Sleeve Top Casual Jumper Pullover Sweater

8. The Trench Vest

Stylish and trendy, trench vests are the best versatile pieces to mix and match into your date night wardrobe as they can be worn over anything from sweaters to dresses. Stick to a trench vest on warmer winter days when you can get away without wearing that bulky jacket!

The trench vest is perfect for winter date night outfits!

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Zeagoo Women's Casual Sleeveless Oversized Open Longline Duster Blazer Jacket Coat Black XL  

9. Go Natural in Neutrals

Dating is all about being natural, so shouldn’t your outfit look it too? Pair your favorite neutral pieces together to create a beautiful soft contrast.

Pairing neutrals together is perfect for winter date night outfits!

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10. Pretty In A Poncho

Easily thrown on over a cute outfit, ponchos add just the right amount of color and warmth to touch up any style!

Ponchos are perfect for winter date night outfits!  Ponchos are perfect for winter date night outfits!

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11. Pair A Bomber Jacket With Your Go-To Look

Whether you’re a little black dress kind of girl or the girl that loves to keep it casual with jeans and sneakers for a winter date, add an edge to your date night attire with a bomber jacket. Bombers easily give that last little touch of flair to step up any simple outfit.

Bomber jackets are so cute for winter date night outfits!  Bomber jackets are so cute for winter date night outfits!

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Bomber jackets are so cute for winter date night outfits!  

12. Bell Sleeves

Add a little flair to your date night attire with the beauty of belle sleeves. These sleeves can instantly dress up any look for a trendy and stylish outfit! Bell sleeves are making a statement in the fashion world lately and are perfect for those winter date night outfits!

Bell sleeves are the perfect touch for winter date night outfits!  Bell sleeves are the perfect touch for winter date night outfits!

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Shopglamla Brushed Hacci Bell Long Sleeves Rayon Top Blouse Hacci Fabric Classic Rose Pink L  

13. A Classic Denim Jacket

Denim does all, toss this timeless piece on over your tee and set off for a lovely adventure. Perfect for those casual dates on warmer days!

Denim is perfect for winter date night outfits!

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Denim is perfect for winter date night outfits!  Denim is perfect for winter date night outfits!

14. Shaggy And Chic

Shag off the winter blues and step up your style in this fabulous statement piece. These chic coats make perfect winter date night outfits because you can easily transform them from day to night!

Shaggy fur coats are perfect for winter date night outfits!  Shaggy fur coats are perfect for winter date night outfits!

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15. A Classic Cardigan

Simple and sweet, what more could you want? Cardigans are a wardrobe staple for every season and give you that extra layer of warmth without weighing down your outfit.

Cardigans are perfect for winter date night outfits!

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16. The Timeless Button Down

Classy, simple and effortless – pair a button down with a statement piece (such as a necklace or cute belt) for an adorable outfit that works for any date.

Simple button down shirts are perfect for winter date night outfits!

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17. The Edgy Leather Jacket Look

Edgy, sexy and stylish, leather jackets are the ultimate piece for amping up any outfit to give you those coooool girl vibes.

Leather jackets are perfect for winter date night outfits!

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18. A Fuzzy Cardigan To Cuddle In

Easily paired with basic pieces, this comfy cardi screams for some date night cuddles (yes please!). Definitely one of the coziest winter date night outfits!

Fuzzy cardigans are perfect for winter date night outfits!  Fuzzy cardigans are perfect for winter date night outfits!

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ASSKDAN Women's Fuzzy Velvet Open Front Loose Fitting Long Jacket Coat with Hood (S, Grey)19. Turtlenecks For The Win

Everyone loves a cute turtleneck, especially these trending vest styles that look amazing worn under leather jackets. Any type of turtleneck will work for winter whether it’s oversized, cropped or a turtleneck dress!

Turtlenecks are perfect for winter date night outfits!

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Turtlenecks are perfect for winter date night outfits!

20. Flirty Florals

Show off your sweet side in a little bit of floral! Feel free to play with your florals and mix and match for a chic yet totally cute look!

Winter florals are perfect for winter date night outfits!  Winter florals are perfect for winter date night outfits!

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21. Fabulous Fringe

Have some fun with fringe! Add a little detail to your wardrobe with some savvy little touches on your fav sweaters. Sometimes it’s the smaller things that make all the difference.

Fringe outfits are perfect for winter date night outfits!

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22. Leather Leggings

Comfort meets style with leather leggings. Easily paired with anything from sweaters to tees, this simple piece is everything you need for a sleek date night outfit.

Leather leggings are perfect for winter date night outfits!

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  Solid Soft Stretch Longline Long Sleeve Open Front Knit Cardigan Burgundy Size M

23. Rock That Oversized Sweater

Guys love a girl that can not only rock fancy little tops but also a girl who can pull off a big sweater and still look gorgeous. This look is a go-to for just that.

Oversized sweaters are perfect for winter date night outfits!  Oversized sweaters are perfect for winter date night outfits!

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24. A Fur Vest

Beat the brrrrrr with fur and add a touch of chic coziness!

Fur vests are perfect for winter date night outfits!

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25. Classy Overcoats

Got the perfect outfit but not sure what to wear through the cold? Look no further than a classy overcoat to tie the whole look together.

Classy overcoats and wool coats are perfect for winter date night outfits!

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Do you have any other suggestions for cute winter date night outfits? Share in the comments below!
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Jozy Caulfield

A twenty something college fashionista pursuing a degree in journalism at the University of Minnesota Twin Cities. Style junkie and blogging obsessed, lover of all things coffee, floral, and pink. Firm believer that travel is the best therapy and happiness is key, follow along with me on my blog and find your bliss at BlondeandBliss.com!

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