Date Night
Dec 24, 2018

The Perfect Winter Date Outfits Do Exist—Here Are 14 of Them

by Dale Arden Chong

Let’s be honest. Getting ready for a date can be stressful enough as it is, but when you also have to consider the frigid weather, it’s a whole new ball game. While you want to put your best sartorial foot forward, you also have to keep in mind that, more likely than not, you’ll be piling on the layers in preparation for the temperatures outside. Fortunately, just because it’s cold out doesn’t mean you have to compromise your personal style for the sake of overall comfort. In fact, there are plenty of winter date outfits that’ll give you the best of both worlds, and who could turn away from that?

To illustrate our point, we’ve rounded up some of the best cold weather–appropriate ensembles that are fit for your next date, whether you’re about to enjoy the first of many or adding in some extra quality time with your S.O. this season. Shop them all below.

Polished winter date outfit

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Style Tip: Brighten up a cozy sweater look with a pair of white trousers.

Ribbed Cashmere Sweater

We love a subtle off-shoulder detail.

Simple winter date outfit

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@camillecharriere

Style tip: You can't go wrong with a chic turtleneck dress and classic earrings.

You'll wear these for years.

Winter date outfit with leather leggings

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@courtneeruthie

Style Tip: Opt for leather leggings and a comfortable pullover for a more casual look.

These make quite the statement.

Chic going-out date outfit

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Style Tip: Pair a classic blazer with patent pants to create a cool ensemble for a night out.

Elegant winter date outfit

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Style Tip: Nothing will feel chicer than a longline coat, a funnel-neck sweater, and wide-leg pants.

Tailored Longline Coat

This will keep you protected from the wind.

Fisherman sweater winter date outfit

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@double3xposure

Style Tip: A fisherman sweater will feel instantly polished with a slip skirt.

Contrasting Knit Sweater

A fisherman sweater is always good for the season.

Naropa Slip Skirt

Never say no to a slip skirt.

Winter date outfit with faux-fur jacket

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Style Tip: Brave the cold with a chic faux-fur jacket and a pair of white jeans.

This will always look good.

Winter date outfit with colorful faux-fur jacket

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Style Tip: A playful faux-fur jacket will dress up a casual pair of jeans and a tee.

Shearling coat winter date outfit

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@humidityistheenemy

Style Tip: When the weather gets colder, add a shearling coat and a pair of tights to your ensemble for more warmth.

Winter date outfit with skirt

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@karenbritchick

Style Tip: Yes, you can wear a denim midi skirt for winter. Just style it with a simple turtleneck and boots.

Red winter date outfit

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Style Tip: An all-red outfit will stand out unlike any other.

Temperley London

Vera Patent Coat

The texture of this is everything.

Monochrome purple date outfit

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Style Tip: Get tonal this winter for a fresh take on monochrome dressing.

Maurier Sweater

Who could pass up this sweater?

Winter date outfit with dress and boots

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Style Tip: A long-sleeve dress with a pair of tights and slouchy boots will never do you wrong.

Kate Leather Knee Boots

Slouch boots are major this season.

Casual winter date outfit

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@waityouneedthis

Style Tip: Add a colorful coat to your otherwise neutral outfit for that extra pop.

Leopard-Print Leather Ankle Boots

We're not done with leopard print yet.