44 Winter Boots With Heels in Every Style

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.