Here's What Not to Wear on a Winter Date, From a Matchmaker

Getting dressed for winter dates is like riding the struggle bus over and over again. On one hand, you want to look like the best version of yourself, but on the other hand, you don't know how that's physically possible with all those required layers. Don't worry, people—we've left this one up to an expert. Below, Nora DeKeyser, matchmaker at Three Day Rule, told us exactly what not to wear on a winter date, along with a few outfit ideas to get you inspired. Check out her list below, remember the choice is ultimately up to you and your comfort level (not anyone else's), and click in to see some winter-date outfit ideas.

What Not to Wear: Something too revealing or baggy.

What to Wear: Tights, a dress, and a nice jacket.

What to Wear: Tights

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Collage Vintgae

"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."

What Not to Wear: Baggy Clothes

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Collage Vintgae

"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."

Check out more winter-date outfit ideas:

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Collage Vintgae

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