Winter Outfits
Nov 29, 2023

15 Winter Date Outfit Ideas That Are Cute and Comfortable

by Caitlin Burnett

Date night during the winter months can be a tricky event to navigate. Something you typically look forward to can become something you dread. Trying to put together an outfit that won't leave you feeling cold or uncomfortable but still make you feel like the best version of yourself is a particularly difficult task. Throw a post-pandemic world into the mix, and well, winter date nights really can't be totally spontaneous. The little dress or pretty top you reach for during the warmer months just won't cut it in the wind, rain, or snow.

We're here to help with a slew of outfit ideas that will turn winter date nights into the fun, romantic activities that they're meant to be, even in cold weather. Just because it's cold outside doesn't mean you need to sacrifice your style or relationship building. From leather pants to sweater dresses to belted trench coats, we've got your outfit covered to ensure you feel cute while remaining comfortable.

Whether you're dressing up to safely dine outside or stay in, below are 15 winter date-night outfits that you'll actually want to wear.

What to wear on a winter date

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@femmeblk

On Lydia Tsegay: H&M pants; Zara bag

Leather pants always lend a cool vibe, and a fitted sweater balances out proportions.

Chic winter date outfit ideas

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@deborabrosa

On Débora Rosa: By Malene Birger set

A knit set always looks elevated.

Comfortable winter date outfit ideas

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@frannfyne

On Franny Fyne: Who What Wear Collection bag

This feminine sweater and skirt juxtaposed with edgy combat boots create a perfect balance.

The best winter date outfits

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@nitsanraiter

On Nitsan Raiter: Prada bag; Charlotte Simone coat; I.Am.Gia pants

A furry coat feels especially fun when paired with patent-leather pants and boots.

Winter date outfits

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@eniswardrobe

On Eni Ilori: AllSaints dress

Throw your favorite slip dress over a long-sleeve top of similar color for a sophisticated, monochrome look.

Cute winter date looks

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@thefatgirloffashion

A matching sweater and knit skirt are equal parts cozy and chic.

What to wear on a winter date

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@taniasarin

On Tania Sarin: Carolina Herrera dress

It doesn't get any cooler than a printed maxi dress and knee-high boots.

Winter date outfit ideas

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@spiritedpursuit

On Lee Litumbe: Fendi coat; Dior belt

A belted coat is as timeless as it gets. Throw one on over an all-black outfit for instant polish.

Cute winter date outfit ideas

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@lisadnyc

On Lisa DiCicco Cahue: Helmut Lang Cutout Turtleneck ($175); ReDone '70s High-Rise Jeans ($275)

A cutout sweater adds interest to any outfit.

What to wear on a winter date

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@styledevotee

On Shalini Acharya: & Other Stories sweater; Celine sunglasses; Vince dress; Bottega Veneta Mini Jodie Bag ($1720); Gucci loafers

A cardigan and slip dress are a classic date-night combination. Just throw a coat over it and you're ready for winter.

Cute winter date outfit ideas

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@littleblackboots

On Jill Wallace: LNA Martin T-Shirt ($90)

A belted blazer dress and tights will take you through winter in style.

Comfortable winter date outfits

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@sabinasocol

On Sabina Socol: Miista boots

Never underestimate the power of a cozy sweater, perfectly fitting jeans, and luxe-looking boots.

Winter date outfits

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@nnennaechem

On Nnenna Echem: Bik Bok top

Here's proof you can never go wrong with a hint of sparkle and a red lip.

What to wear on a winter date

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@discodaydream

On Lauren Johnson: Orseund Iris Night-Out Open Back Blouse ($540)

An open-back top is always a good idea for date night, and leather pants make it feel seasonal.

Cute winter date outfit ideas

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@fongminliao

Top off the classic combo of a blazer dress and over-the-knee boots with fun glitter earrings.