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 […]

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, a heel elevates your look while also subtly changing the overall vibe. I always walk a bit taller and notice my posture improve 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 25 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 ($395). Little block-heel boots make tailored trousers look even more polished.

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

On Amy Lefévre: Strathberry bag, Schutz Abbey Boots ($238). The only thing that can make a jumpsuit cooler is a pair of heeled boots. 

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 get taken up a notch with the addition of heeled ankle boots.

On Débora Rosa: Full Mango look. 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. 

On Ada Oguntodu: Ankle boots. A cool outfit gets even cooler with a sleek heeled ankle boot. 

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

On Natasha Ndlovu: Alexander McQueen Ribbed Coat ($1740); 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. 

On Yamila Orozco: Trousers and ankle boots. The classic combination of a turtleneck sweater, trousers, and 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). 

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

On Babba Rivera: Fuzzy coat. Colored coats are always fun, and heeled black ankle boots just make them feel a touch more polished. 

On Amanda Sorenson: White boots. 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 Priscilla Akogyeram: Missguided coat; Prada bag; Zara leggings. A black outfit feels instantly ready for anything with the addition of pumps and a fun coat. 

On Joanna Coops: Pretty Little Thing suit. Wear this outfit on your next date night. 

On Janka Polliani: Gucci bag; Gucci 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 is suddenly an outfit by adding unique heels. 

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

Next: It’s a sweater. It’s a coat. It’s a sweater coat, and I want all of them.

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