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


(Image credit: @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

Winter Boots With Heels Under $250

Winter Boots With Heels Under $500

Winter Boots With Heels Over $500

Next: 6 Fall Boot Trends That Are Already Selling Like Crazy

Jasmine Fox-Suliaman

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.