If You Are Going to Wear Heels This Winter, This Is How to Do It

During the freezing temperatures of winter, there are few things that matter more than comfort. Staying warm and cozy is priority number one, so footwear is typically just a means to an end of this quest. Sneakers and thick boots are on heavy rotation (and for good reason!), but there are those rare occasions when you feel like your outfit needs a bit more polish, and suddenly, heels are back in the mix. 

Whether in pump or boot form, heels elevate your look while also subtly changing the overall vibe. I always walk a bit taller and notice my posture improves after slipping on a pair of heels. They make me feel confident and ready to take on whatever I have on my agenda. Wearing heels in the winter can be a bit trickier given the weather conditions, so pairing them with the right outfit is key. I usually opt for heeled boots to ensure warmth, but pumps and mules can also work with the right outfit. Below are 24 genius winter outfits with heels to try this season when you're ready to give your sneakers a break. 

The best winter outfits with heels

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@chrissyford

On Chrissy Rutherford: BY FAR bag

Leather pants and black boots are always a winning combo. 

Winter outfits with heels to try

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@missenocha

On Enocha Tellus: Zara boots

It doesn't get chicer than a textured sweaterdress and knee-high heeled boots. 

On Alyssa Coscarelli: Staud Large Moon Bag 

Little block-heel boots make tailored trousers look even more polished.

On Imani Randolph: For Love & Lemons dress

Hello, date-night look!

Winter outfits with heels to try this season

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@lefevrediary

On Amy Lefévre: Strathberry bag, Schutz boots

The only thing that can make a jumpsuit cooler is a pair of heeled boots. 

Cool winter outfits with heels

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@aimeesong

On Aimee Song: Chloé bag

When in doubt, go monochrome. 

On Bettina Looney: Bottega Veneta The Pouch Large Clutch ($2700)

Make your favorite heels work for winter by adding opaque tights. 

On Ellie: Stand Studio coat; Saks Potts pants; Charles & Keith shoes, Le Specs The Last Lolita Sunglasses ($119)

Mixing prints and bold colors gets taken up a notch with the addition of heeled ankle boots.

Winter outfit ideas with heels

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@deborabrosa

On Débora Rosa: Mango outfit

Make a Canadian tuxedo even cooler with black heeled ankle boots (and maybe throw a big coat on top when heading out). 

Chic winter outfits with heels

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@anoukyve

On Anouk Yve: Jimmy Choo boots; Little Lifner bag

Dress up your favorite coat and thick scarf with a pair of knee-high heeled boots. 

Winter outfit ideas to wear with heels

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@ada_oguntodu

A cool outfit gets even cooler with sleek heeled ankle boots. 

Cool winter outfits with heels

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@emilisindlev

The best way to add a pop of color to an otherwise neutral outfit? Bright-hued heels. 

On Natasha Ndlovu: Alexander McQueen coat; Bottega Veneta Jodie Mini Bag ($1720)

Your favorite sweaterdress was made to be paired with pumps. 

On Renia Jaz: Bottega Veneta The Chain Pouch ($3600)

Camel always looks expensive—even more so when paired with neutral-colored pumps. 

Cool winter outfits with heels

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@dolcecurvy

The classic combination of a turtleneck sweater, trousers, and a black coat suddenly feels modern when styled with heeled black ankle boots. 

On Lorna: Polène bag

Give your favorite blazer-and-skinny-jeans outfit a fun twist with heeled boots (bonus points if they're snake print). 

Winter outfit ideas to wear with heels

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@smythsisters

On Marianne: Levi's jeans

The perfect dinner-at-home look includes a white button-down, black jeans, heeled boots, and a chunky scarf. 

The best winter outfits with heels

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@babba

Colored coats are always fun, and heeled black ankle boots just make them feel a touch more polished. 

White heeled boots were made to be worn with plaid coats. 

Cool winter outfit ideas with heels

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@femmeblk

On Lydia Tsegay: Polène bag; Zara T-shirt; Sentaler coat

Strappy heels with an all-white look are as aspirational as it gets. 

Cool winter outfit ideas with heels

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@polliani

On Janka Polliani: Gucci bag and Off-White Tights ($120)

This feels like a modern-day Blair Waldorf outfit—in a good way. 

Chic winter outfits with heels

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@ileniatoma_

On Ilenia Toma: Gucci GG Marmont Mini Bag ($950)

Note to self: Invest in tights. 

Winter outfit ideas to wear with heels

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@greceghanem

On Grece Ghanem: Zara blazer

A simple blazer and jeans are suddenly an outfit with the addition of unique heels. 

The best winter outfits with heels

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@styleheroine

On Evangelie Smyrniotaki: Woolrich jacket

Slightly baggy jeans feel balanced with a lift from sleek pumps. 

Shop Heels

Nude heels are something you can always rely on.

I'm surprised this pair is still in stock.

These come in five colors for you to choose from.

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