21 Winter Date Outfit Ideas That Are Cute and Comfortable

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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. 

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@deborabrosa

On Débora Rosa: By Malene Birger set

A knit set always looks elevated. 

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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. 

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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. 

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@thefatgirloffashion

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

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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. 

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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.

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@monikh

On Monikh Dale: Christoper Esber Convertible Ribbed Dress ($880)

A ribbed-knit dress with cutout detail is guaranteed to garner compliments. 

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@endlesslyloveclub

On Jen Ceballos: Prada boots; Nisse Eiko Leather Trench Dress ($380)

A leather dress is cool on its own, and adding knee-high boots just doubles down on that fact. 

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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. 

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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. 

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@littleblackboots

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

A belted blazer dress can go from fall to winter with the simple addition of tights.

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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. 

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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.

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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.

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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.

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@fongminliao

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

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@fashionenth

A turtleneck-blazer combination is a classic, so pairing the pieces with leather pants and boots keeps the look feeling special. 

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@emilisindlev

On Emili Sindlev: A.W.A.K.E. Mode Vegan Leather Skirt ($680)

Although you may need to add a coat, the pairing of a sweater and leather skirt is one perfect outfit. 

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@slipintostyle

On Ellie: The Frankie Shop Pernille Oversize Blazer ($240)

Not only is a tailored suit classic, but it's also ultra-comfortable. Just add heels to make it feel date night–ready.

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@dolcecurvy

On Yamila Orozco: Violeta by Mango blazer

Make your leather shorts work for winter by layering them over sheer tights for a night out.