Call Me Crazy, But I Only Want to Wear Winter Boots With Heels

best winter boots with heels


@nickslaboratory for @fashionwithjazz; STYLING: Urban Outfitters Salmon Rounded Rectangle Sunglasses ($20); Staud Nat Top ($145); Zara Belted Faux Leather Pants ($26); Dolce Vita Kelsie Booties in Ivory Croc Print Leather ($120); Mlouye Mini Lantern Bag Pleated ($460)

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.

Knee-high snakeskin boots? Yes, please.

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.

More chunky boots for your enjoyment.

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. 

These Aldo shoes are as slick as frost itself.

Now, these are winter boots with heels that you can wear every day.

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.

We live for kitten-heel boots, and this pair from Coach is giving us life.

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.

As I said before, leather legs (like thigh-high and over-the-knee boots) are having their moment again. And I can’t think of a more on-trend boot than this ruched version from Louise et Cie.

Chunky Chelsea boots are big this seasonbut 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.

Winter whites soar to new heights with these beautiful boots from Raye.

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.

The see-through heel on this Simon Miller boot is what sold me.

You really can’t go wrong with a black patent winter bootie.

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.

Suede knee-high boots are a must in any wardrobe.


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.