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 Imani Randolph: For Love & Lemons dress
Hello, date-night look!
On Aimee Song: Chloé bag
When in doubt, go monochrome.
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 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 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.