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. 

The best winter outfits with heels


Photo:

@chrissyford

On Chrissy Rutherford: BY FAR bag

Leather pants and black boots are always a winning combo. 

Shop the key piece:

BY FAR Este 25mm Square Toe Ankle Boots

BY FAR

Este 25mm Square Toe Ankle Boots

$484

Winter outfits with heels to try


Photo:

@missenocha

On Enocha Tellus: Zara boots

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

Shop the key piece:

Staud Cami Boot Tan Suede

Staud

Cami Boot Tan Suede

$550

Chic winter outfits with heels


Photo:

@alyssainthecity

On Alyssa Coscarelli: Staud Large Moon Bag 

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

Winter outfits with heels to try this season


Photo:

@lefevrediary

On Amy Lefévre: Schutz boots

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

Shop the key piece:

Tony Bianco Fantasy Butter Nappa 8cm Calf Boots

Tony Bianco

Fantasy Butter Nappa 8cm Calf Boots

$360

How to wear heels in the winter


Photo:

@champagnemani

On Imani Randolph: For Love & Lemons dress

Hello, date-night look!

Shop the key piece:

Zara Zippered Heeled Ankle Boots

Zara

Zippered Heeled Ankle Boots

$90

Cool winter outfits with heels


Photo:

@aimeesong

On Aimee Song: Chloé bag

When in doubt, go monochrome. 

Shop the key piece:

Free People Rocky Slouch Boots

Free People

Rocky Slouch Boots

$298

Chic winter outfits with heels


Photo:

@bettinalooney

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:

Jimmy Choo Bing Crystal Embellished Patent Mule

Jimmy Choo

Bing Crystal Embellished Patent Mule

$995

The best winter outfits with heels


Photo:

@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.

Shop the key piece:

Vince Camuto Quindele Pointed Toe Bootie

Vince Camuto

Quindele Pointed Toe Bootie

$159

Winter outfit ideas with heels


Photo:

@deborabrosa

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). 

Shop the key piece:

Mango Block Ankle Boots With Square Toe

Mango

Block Ankle Boots With Square Toe

$70

Shop the key piece:

Vicenza Friday Fever Heel Boots

Vicenza

Friday Fever Heel Boots

$248

Winter outfit ideas to wear with heels


Photo:

@ada_oguntodu

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

Shop the key piece:

Staud Wally Ankle Boots

Staud

Wally Ankle Boots

$395

Cool winter outfits with heels


Photo:

@emilisindlev

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

Shop the key piece:

Jeffrey Campbell Estella Pointed Toe Slingback Pump

Jeffrey Campbell

Estella Pointed Toe Slingback Pump

$145

The best winter outfits with heels


Photo:

@natashandlovu

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:

Sam Edelman Bianka Slingback Pump

Sam Edelman

Bianka Slingback Pump

$140

Cool winter outfits with heels


Photo:

@dolcecurvy

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:

Tory Burch Double T Ankle Boot

Tory Burch

Double T Ankle Boot

$478

Winter outfit ideas with heels


Photo:

@venswifestyle

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:

Aeyde Melia Leather Point-Toe Pumps

Aeyde

Melia Leather Point-Toe Pumps

$395

Winter outfits with heels to try this season


Photo:

@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). 

Shop the key piece:

Reformation Remy Knee Boot

Reformation

Remy Knee Boot

$478

Winter outfit ideas to wear with heels


Photo:

@smythsisters

On Marianne: Levi’s jeans

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

The best winter outfits with heels


Photo:

@babba

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

Shop the key piece:

Madewell The Dimes Kitten-Heel Boot

Madewell

The Dimes Kitten-Heel Boot

$198

Winter outfits with heels to try


Photo:

@amandasorensonn

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

Shop the key piece:

Mango Round-Toe Leather Boots

Mango

Round-Toe Leather Boots

$250

Cool winter outfit ideas with heels


Photo:

@femmeblk

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:

Stuart Weitzman Nudistcurve 100 Smooth Leather Sandal

Stuart Weitzman

Nudistcurve 100 Smooth Leather Sandal

$475

Cool winter outfit ideas with heels


Photo:

@polliani

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:

Charles & Keith Black Gabine Patent Leather Mules

Charles & Keith

Black Gabine Patent Leather Mules

$83

Chic winter outfits with heels


Photo:

@ileniatoma_

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

Note to self: Invest in tights. 

Shop the key piece:

Steve Madden Lizah Knee High Boot

Steve Madden

Lizah Knee High Boot

$100

Winter outfit ideas to wear with heels


Photo:

@greceghanem

On Grece Ghanem: Zara blazer

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

Shop the key piece:

Manolo Blahnik Hangisimu 70 Embellished Satin Mules

Manolo Blahnik

Hangisimu 70 Embellished Satin Mules

$1095

Classic.

The best winter outfits with heels


Photo:

@styleheroine

On Evangelie Smyrniotaki: Woolrich jacket

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

Shop the key piece:

Zara High Heeled Shoes

Zara

High Heeled Shoes

$50

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



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