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!
Sexy but sweet, the ultimate go-to for a casual dinner date or trip to the movies.
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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.
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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!
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!
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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.
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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!
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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!
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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!
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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.
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Easily thrown on over a cute outfit, ponchos add just the right amount of color and warmth to touch up any style!
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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.
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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!
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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!
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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!
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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.
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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.
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Edgy, sexy and stylish, leather jackets are the ultimate piece for amping up any outfit to give you those coooool girl vibes.
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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!
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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!
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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!
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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.
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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.
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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.
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Beat the brrrrrr with fur and add a touch of chic coziness!
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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.
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