Here's What Not to Wear on a Winter Date, From a Matchmaker
"The first thing not to wear on a winter date is something too revealing! The last thing you want to do on a first date is feel uncomfortable and overexposed. People often make the mistake of thinking 'sexy' is analogous to showing skin, which is really not the case. 'Sexy' is when you look and feel confident, according to the temperature outside! Don't skip out on the tights just because it's a first date! You will look sexier if you are comfortable and warm enough to walk outside."
"The second thing not to wear on a winter date is baggy clothes. At the same time that you want to feel comfortable and warm enough for the temperature outside, you also aren't going snowboarding. So still show your curves! I recommend a dress with tights and a nice jacket."
Blazer + Sweater + Printed Pants
Adding printed pants to your date night outfit is the perfect way to stand out.
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Collage Vintage
Suede Jacket + Miniskirt + Tights + Statement Shoes
Don't put away your miniskirt just because it's winter. Add a pair of black tights instead, paired with your favorite statement heels for a sophisticated look.
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Collage Vintgae
Parka + Sweaterdress + Tights + Over-the-Knee Boots
You can never go wrong with a sweaterdress and over-the-knee boots. This look is both comfortable, attractive, and don't forget warm.
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Collage Vintage
Leather Jacket + Knit Midi Skirt + Boots
Add a leather jacket to any look to make it date night–appropriate.
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Collage Vintgae
Faux-Fur Jacket + Tweed Minidress + Tights + Boots
Add a flirty vibe to your tweed minidress by pairing it with your favorite ankle boots and faux-fur jacket. Don't forget the tights for warmth!
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Collage Vintage
Shearling Jacket + Long-Sleeve Shirt + Slip Dress
If you're looking for a bolder option, try pairing a slip dress with an oversize shearling coat.
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Collage Vintgae
Furry Coat + Maxi Dress + Sneakers
A furry coat is a winter staple. Paired with a maxi dress and sneakers, this chic look screams winter date-night style.
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Collage Vintgae
Bomber Jacket + Sweaterdress + Pumps
Pair your go-to dress and heels look with a bomber jacket for a more casual approach to your date-night look.
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Collage Vintgae
Check Coat + Turtleneck + Jeans + Sneakers
For the ultimate casual-cook look, pair your favorite statement coat with a turtleneck and jeans for a chic winter date outfit.
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Collage Vintgae
Minidress + Tights + Coat + Boots
Not revealing or baggy, this outfit follows the winter outfit formula rules perfectly by adding a touch of personality to a chic tights-and-dress look.
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Collage Vintgae
Oversize Scarf + Jacket + Shirt + Coated Pants + Patent Boots
Try an oversize scarf with an edgier outfit for a standout look.
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Collage Vintgae
Leather Jacket + Knit Dress + Boots
Animal print is so on trend right now. Pair a printed dress with a leather jacket and your favorite black ankle boots for a fashion-forward outfit.
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Collage Vintage
Tailored Coat + Sweater + Trousers + Nude Heels
Try an all-nude outfit for a light, sophisticated look.
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Collage Vintgae
Tailored Jacket + Tights + Heels
Pairing black tights with black heels is the perfect way to accentuate the natural line of your legs. Add a tailored jacket to finish off this look.
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Collage Vintgae
Coat + Sweaterdress + Skinny Jeans + Chunky Boots
Following Nora's rule, wearing tights, dress, and a nice coat is the perfect winter-date outfit formula. Add a pair of on-trend boots to complete the look.
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Collage Vintage
Cardigan + Minidress + Tights + Flat Boots
Make your favorite summer look winter-appropriate by adding a long cardigan and tights.
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Collage Vintgae
Blazer + Trousers + Pumps
You can never go wrong with this classic all-black look.
This post was originally published at an earlier date and has since been updated. Next up, shop everything we're craving for a stylish winter.