Let's Do This: 30 Winter Heels for Every Budget and Occasion
While you may not automatically associate winter with heels, turns out they actually make a lot of sense together. Once winter arrives, the flats and thin-soled heels you were pounding the pavement in no longer serve your need for warmth, and the thicker the sole, the better. And with the return of holiday parties and work soirées, you’ll want to invest in a few good pairs to go with your festive outfits all season. Personally, I find the winter heel superior to its sandal counterpart because of the built-in comfort level of boots and close-toed shoes generally. Another benefit is their ability to dress up even the most mundane of outfits, even sweats.
This winter, the assortment of winter-appropriate heels is vast and includes everything from the trusted kitten-heel and ankle-boot styles to more niche styles like the loafer heels and Mary Janes. Most styles can be worn casually and also dressed up, making them great options if you’re looking to splurge on only a couple of pairs this year. Keep scrolling for the best picks from across the internet in every category and for every occasion.
Knee-High Boots
Knee-high boots are a forever classic that can be worn year-round, so it's a category worth investing in, as they literally go with everything. Take this outfit, for example. Here, the boots look so chic and cozy paired with fleece and a fuzzy hat. In the spring, wear the same pair with a flowy minidress, and they will look like completely different boots.
Shop knee-high boots:
Ankle Boots
This outfit proves your legs don't have to hibernate just because it's cold outside. It's always a good time to put on some ankle boots, show some leg (with tights, of course), and see what the streets are talking 'bout.
Shop ankle boots:
These square-toe boots will quickly dress up your jeans, and also make great shoes for the office.
Heeled Loafers
The intersection of prep and punk is so 2021 and has come to a head in the heeled-loafer trend. Go preppy and pair them with your argyle sweaters and button-downs one day, and the next, trade your prep for leather pieces to edge things up.
Shop heeled loafers:
If your winter aesthetic is leaning retro, these are the pair for you. They also feel very Gucci.
Platforms
Platforms are truly in the spotlight this season. Aside from the practical value of a platform shoe in the winter, this shape can add some much-needed drama to your outfit.
Shop platforms:
These platform heels don't click-clack; they stomp. Energy.
These are going to look adorable with patterned tights underneath.
Wear these in lieu of pants.
Mary Janes
This '90s punk-princess classic has remerged and is having a moment in 2021. I've seen fashion girls wearing them with everything from midi skirts to jeans and styling them in every way from Gwen Stefani to school girl. Layer some graphic tights underneath for an element of surprise.
Shop Mary Janes:
Absolutely love this shape. I'd wear these with a tuxedo suit.
Heeled Cowboy Boots
I too have been stomping around in my cowboy boots all spring and summer and am not planning on changing anything this winter. Look for a pointed toe and kitten heel to elevate the inherent casualness of the shape.
Shop heeled cowboy boots:
Clogs
I've finally bought in to the clog movement solely because of all the cool options out there right now. This undeniably comfortable and warm shoes are a dream in cold weather and also a touch quirky, which is right up my alley. Reach for these when you want to shake things up a bit in your rotation—they won't disappoint.
Shop clogs:
Next up, All My Friends Are Getting Married—Here's What I'm Wearing to Match Each Vibe
-
Laura Harrier Keeps Wearing the "Dated" Shoe Trend I Bet Will Make a Huge Comeback in 2025
French women agree.
By Eliza Huber
-
J.Lo Wore the Brand-New Uggs That'll Go Viral and Sell Out By December 1—Guaranteed
Don't say I didn't warn you.
By Eliza Huber
-
Zoë Kravitz Just Wore the One Winter Boot Trend That Every Chic Celeb Agrees On
Dakota Johnson and Sofia Richie are also fans.
By Nikki Chwatt
-
Katie Holmes Just Wore the Elegant Boot Color New Yorkers Are Abandoning Black For
Take note.
By Nikki Chwatt
-
I Thought This Heel Trend Was Dated, But These Celebrity Outfits Just Changed My Mind
Consider me convinced.
By Natalie Munro
-
Black Shoes, Watch Out—This Alternative Color Is Chicer, More Elegant, and Just as Classic
Brown *just might* be the new black.
By Copelyn Bengel
-
Elizabeth Olsen Just Wore the Only Boot Trend That's Sensible for the Airport
I'm taking notes.
By Natalie Munro
-
My Friend Wants to Elevate Her Wardrobe—I Sent Her These 31 Nordstrom Fall Sale Finds
All have closet-staple status.
By Jennifer Camp Forbes