Any one of my colleagues can attest that prior to COVID-19, they rarely spotted me in anything but heels. And while some comfy shoes can occasionally lure me from my love for inches of elevation, I find that my cart still remains filled with winter boots with heels coming into the colder months. For me, come rain or shine, there’s no other style of shoe I’d rather wear than boots with some height. And I’m not alone in this assessment. With trends like full leather legs dominating the F/W 2020 runways and a plethora of chic thigh-high boot outfits, heeled boots have juxtaposed the rise of athleisure.
For women who relish dressing up just because, being able to slip into a pair of heeled boots has brought a little sliver of comfort in this time of unprecedented changes. And while you may not be able to show off your newest boots yet, who says you can’t treat yourself? We’ve taken the liberty of rounding up the best winter boots with heels to shop at every price point. From practical to downright magical, there’s a pair of boots ahead just for you.
Winter Boots With Heels Under $100
Who knew that the perfect affordable winter boots with kitten heels could be found on Amazon?
There’s nothing else I’d rather wear for the rest of the winter than these platform heeled booties.
PSA: The square-toe boots trend isn’t going anywhere anytime soon, so you’ll want to scoop up this classic pair from Charles & Keith.
If you’re anything like me, cowboy boots have been at the top of your list since Fendi debuted their iterations back in F/W 2018. Now that you’ve found the perfect affordable pair, you’ll just need to style them right.
I’ve been obsessed with two-tone boots for quite some time but have been unable to find an affordable pair—until now.
Calling all block-heel lovers: Topshop’s Western-shaped crocodile boot is the winter footwear you’ve been dreaming of since last year.
Winter Boots With Heels Under $250
It may be cold outside, but these Vince Camuto boots sure are piping hot.
Mango’s heeled boot section always low-key slays. Case in point? These leather-and–faux-fur ankle boots.
This may be a controversial pick, but I’ll take the flack because Timberlands have always been the boot (even Kamala Harris agrees). We love this heeled version of the winter boot staple.
Chunky Chelsea boots are big this season, but if you’re a stickler for height, then opt for the winter staple with heels.
Honestly, Steve Madden never fails to create drool-worthy shoes. These cognac patent winter heeled boots are no exception.
It’s not hyperbole to say that I’ve been unable to stop thinking about these wild boots since I first saw them. I can pull out the text receipts to prove my adoration need be.
I stopped scrolling the second I spotted these biscuit leather booties from Franco Sarto. The hue alone makes them worth adding to your wardrobe.
Don’t worry—you don’t have to wear stiletto boots to get the full effect. Opting for a pair of smaller block-heel winter boots like these Schutz ones will still do the trick.
Winter Boots With Heels Under $500
Any shoes trying to win the title of "statement boots” will now have to fight this pair of Kat Maconie heeled ankle booties for the title.
These chocolate-brown winter boots are too scrumptious to pass up.
I’ve been obsessed with Alohas’s boots for quite some time now, as they make the perfect staple winter boots with heels.
These boots, your living room, and a glass of champagne make for the perfect holiday plans, am I right?
If finding a winter boot with heels in your size has been an issue, I’m here to tell you that Good American’s new shoe line has got you covered.
I’m a sucker for a sculptural heel, especially if it’s in boot form.
Still think the perfect pair of white winter heeled boots does not exist?
A knee-high embroidered winter boot that can be worn well into spring? Don’t mind if I do.
Winter Boots With Heels Over $500
Cult Gaia’s shoes always kill me, and these sculptural heeled booties have me in shambles.
You don’t have to sacrifice your comfort or your heels this winter. Just opt for a pair of classic boots from a luxury footwear company founded by a former podiatric surgeon Marion Parke.
Chelsea Paris is the Black-owned luxury shoe brand on my wish list this season.
Staud’s patchwork knee-high boots sold out immediately when they first came out, so you’ll want to scoop these up stat.
Brother Vellies never fails to create boots that will haunt me.
Have you ever seen a more beautiful tri-color boot? I’ll wait…
I love discovering new brands, and since stumbling upon the sustainable London-based bespoke footwear brand Tabitha Ringwood, I’ve been unable to stop thinking about these boots.
Investing in a nude winter ankle boot from Sarah Flint is never a bad idea.
Who needs a club with a disco ball when you can have these sparkily Dear Frances boots?
If you’ve made it this far, you have a sense that in addition to practical boots, I’m always one to obsess over a beautifully made boot. These Nicholas Kirkwood boots take the cake.
Jasmine Fox-Suliaman is a fashion editor living in New York City. What began as a hobby (blogging on Tumblr) transformed into a career dedicated to storytelling through various forms of digital media. She started her career at the print publication 303 Magazine, where she wrote stories, helped produce photo shoots, and planned Denver Fashion Week. After moving to Los Angeles, she worked as MyDomaine's social media editor until she was promoted to work across all of Clique's publications (MyDomaine, Byrdie, and Who What Wear) as the community manager. Over the past few years, Jasmine has worked on Who What Wear's editorial team, using her extensive background to champion rising BIPOC designers, weigh in on viral trends, and profile stars such as Janet Mock and Victoria Monét. She is especially interested in exploring how art, fashion, and pop culture intersect online and IRL.