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.
On Chrissy Rutherford: BY FAR bag
Leather pants and black boots are always a winning combo.
Shop the key piece:
On Enocha Tellus: Zara boots
It doesn't get chicer than a textured sweaterdress and knee-high heeled boots.
Shop the key piece:
On Alyssa Coscarelli: Staud Large Moon Bag
Little block-heel boots make tailored trousers look even more polished.
Shop the key piece:
On Amy Lefévre: Schutz boots
The only thing that can make a jumpsuit cooler is a pair of heeled boots.
Shop the key piece:
On Imani Randolph: For Love Lemons dress
Hello, date-night look!
Shop the key piece:
On Aimee Song: Chloé bag
When in doubt, go monochrome.
Shop the key piece:
On Bettina Looney: Bottega Veneta The Pouch Large Clutch ($2700)
Make your favorite heels work for winter by adding opaque tights.
Shop the key piece:
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.
Shop the key piece:
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).
Shop the key piece:
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.
Shop the key piece:
A cool outfit gets even cooler with sleek heeled ankle boots.
Shop the key piece:
The best way to add a pop of color to an otherwise neutral outfit? Bright-hued heels.
Shop the key piece:
On Natasha Ndlovu: Alexander McQueen coat; Bottega Veneta Jodie Mini Bag ($1720)
Your favorite sweaterdress was made to be paired with pumps.
Shop the key piece:
The classic combination of a turtleneck sweater, trousers, and a black coat suddenly feels modern when styled with heeled black ankle boots.
Shop the key piece:
On Renia Jaz: Bottega Veneta The Chain Pouch ($3600)
Camel always looks expensive—even more so when paired with neutral-colored pumps.
Shop the key piece:
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).
Shop the key piece:
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.
Shop the key piece:
Colored coats are always fun, and heeled black ankle boots just make them feel a touch more polished.
Shop the key piece:
White heeled boots were made to be worn with plaid coats.
Shop the key piece:
On Lydia Tsegay: Polène bag; Zara T-shirt; Sentaler coat
Strappy heels with an all-white look are as aspirational as it gets.
Shop the key piece:
On Janka Polliani: Gucci bag and Off-White Tights ($120)
This feels like a modern-day Blair Waldorf outfit—in a good way.
Shop the key piece:
On Ilenia Toma: Gucci GG Marmont Mini Bag ($950)
Note to self: Invest in tights.
Shop the key piece:
On Grece Ghanem: Zara blazer
A simple blazer and jeans are suddenly an outfit with the addition of unique heels.
Shop the key piece:
Classic.
On Evangelie Smyrniotaki: Woolrich jacket
Slightly baggy jeans feel balanced with a lift from sleek pumps.
Shop the key piece:
This post was originally published at an earlier date and has since been updated.