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

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
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.
Winter Boots With Heels Under $250
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 season, but if you’re a stickler for height, then opt for the winter staple with heels.
Winter Boots With Heels Under $500
Winter Boots With Heels Over $500
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.
Next: 6 Fall Boot Trends That Are Already Selling Like Crazy

Jasmine Fox-Suliaman is a freelance writer and editor living in New York City. What began as a pastime (blogging on Tumblr) transformed into a lifelong passion for unveiling the connection between fashion and culture on the internet and in real life. Over the last decade, she's melded her extensive edit and social background to various on-staff positions at Who What Wear, MyDomaine, and Byrdie. More recently, she’s become a freelance contributor to other publications including Vogue, Editorialist, and The Cut. Off the clock, you can find her clutching her cell phone as she's constantly scrolling through TikTok and The RealReal, in search of the next cool thing.
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