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 in this quest. Sneakers and thick boots are on heavy rotation (and for a 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. 


(Image credit: @chrissyford)

On Chrissy Rutherford: BY FAR bag

Leather pants and black boots are always a winning combo. 

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(Image credit: @missenocha)

On Enocha Tellus: Zara boots

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

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(Image credit: @alyssainthecity)

On Alyssa Coscarelli: Staud Large Moon Bag 

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

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(Image credit: @lefevrediary)

On Amy Lefévre: Schutz boots

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

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(Image credit: @champagnemani)

On Imani Randolph: For Love & Lemons dress

Hello, date-night look!

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(Image credit: @aimeesong)

On Aimee Song: Chloé bag

When in doubt, go monochrome. 

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(Image credit: @bettinalooney)

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

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

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(Image credit: @slipintostyle)

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.

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(Image credit: @deborabrosa)

On Débora Rosa: Mango outfit

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

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(Image credit: @anoukyve)

On Anouk Yve: Jimmy Choo boots; Little Liffner bag

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

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(Image credit: @ada_oguntodu)

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

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(Image credit: @emilisindlev)

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

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(Image credit: @natashandlovu)

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

Your favorite sweaterdress was made to be paired with pumps. 

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(Image credit: @dolcecurvy)

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

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(Image credit: @venswifestyle)

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

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

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(Image credit: @symphonyofsilk)

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). 

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(Image credit: @smythsisters)

On Marianne Smyth: Levi's jeans

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

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(Image credit: @babba)

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

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(Image credit: @amandasorensonn)

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

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(Image credit: @femmeblk)

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

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

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(Image credit: @polliani)

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

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

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(Image credit: @ileniatoma_)

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

Note to self: Invest in tights. 

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(Image credit: @greceghanem)

On Grece Ghanem: Zara blazer

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

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(Image credit: @styleheroine)

On Evangelie Smyrniotaki: Woolrich jacket

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

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This post was originally published at an earlier date and has since been updated.

Caitlin Burnett
Contributing Editor