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 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.

On Chrissy Rutherford: BY FAR bag. Leather pants and black boots are always a winning combo.

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 Amy Lefévre: Strathberry bag, Schutz boots. The only thing that can make a jumpsuit cooler is a pair of heeled boots.

On Imani Randolph: For Love & Lemons dress. Hello, date-night look!

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.

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).

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.

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

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.

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

On Renia Jaz: Bottega Veneta The Chain Pouch ($3600). Camel always looks expensive—even more so when paired with neutral-colored pumps.

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).

On Marianne: Levi's jeans. The perfect dinner-at-home look includes a white button-down, black jeans, heeled boots, and a chunky scarf.

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.

On Lydia Tsegay: Polène bag; Zara T-shirt; Sentaler coat. Strappy heels with an all-white look are as aspirational as it gets.

On Janka Polliani: Gucci bag and Off-White Tights ($120). This feels like a modern-day Blair Waldorf outfit—in a good way.

On Ilenia Toma: Gucci GG Marmont Mini Bag ($950). Note to self: Invest in tights.

On Grece Ghanem: Zara blazer. A simple blazer and jeans are suddenly an outfit with the addition of unique heels.


On Evangelie Smyrniotaki: Woolrich jacket. Slightly baggy jeans feel balanced with a lift from sleek pumps.

This post was originally published at an earlier date and has since been updated by Jasmine Fox-Suliaman.

Next: According to My Research, These Are the Only 6 Winter Shoe Trends That Matter

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