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:
A classic shape and style you'll be wearing for years to come.
These look way more expensive than they are.
The slouchy fit will only get better with time.
Texture goals.
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.
How sweet are these! Now look at the price…
These are a great deal.
These are hard.
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:
XOXO, Gossip Girl.
Lots of drama.
Exaggerated proportions are my vibe right now.
The silver hardware is such a nice touch.
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.
These are chic and look super comfy.
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:
I just know these are super comfortable.
The double strap is so cute.
Absolutely love this shape. I'd wear these with a tuxedo suit.
For this price, you might as well.
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:
I wouldn't change a thing about these. An instant classic.
Snag a pair while they're still available.
This suede looks super rich.
If I were to be in a Western shootout, I'd definitely wear these.
To spice up your denim looks.
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:
Leave it to UGG to make the coziest heels ever.
Added height without sacrificing comfort.
This chestnut color makes me feel warm from here.
The dramatics.
Next up, All My Friends Are Getting Married—Here's What I'm Wearing to Match Each Vibe
-
When Traveling to Europe, This Dress Trend and Heel Trend Will Ensure You Don't Look Out of Place -
The Pretty Dress Trend L.A. It Girls Are Bringing Into Fall (and the "Basic" Style They Already Forgot About)It's finally time to part ways with boring linen dresses.
-
I'm Manifesting a Fashionable Fall in NYC With These 36Replica Store Anniversary Sale FindsFrye, AllSaints, Vince, Coach, and more.
-
This Is the Classic Black Shoe Tasteful Dressers Wear With Jeans and a White Tee to Make Them Look ChicAs seen on Molly Gordon.
-
I Thought Wearing These Shoes With Shorts Was Cringey—Turns Out the Combo Is Peak 2025Apologies are in order.
-
This Is, By Far, the Sexiest Shoe Trend to Wear With Jeans Right NowSee and shop the style inside.
-
Fall Is Already on My Mind—I'm Prepping My Wardrobe With These 31 ElevatedReplica Store FindsEach piece is chic and on sale.
-
Katie Holmes Is Already Wearing the Boho Boot Color Trend Fashion People Everywhere Will Wear This FallNot once, but twice.
