27 Pairs of Boots with Heels That Even a Podiatrist Would Approve Of

I’m a bit obsessed with finding the best, most comfortable heel. Whether they’re slingbacks, ballet pumps or wedding guest shoes, I am always looking for the perfect intersection of fashion and function. They need to be walkable with a super plush insole—but also, not look orthopedic. With fall just around the corner, I consulted a podiatrist and asked them to share the qualities they’d look for in boots with heels that’ll look great without killing my feet. From my best overall pick, the Margaux The Edie Boot ($595) to the podiatrist-approved Vionic Nella Boots ($190; $119) and celeb-approved Larroudé Kate Boots ($485; $283), here are 27 pairs of boots with heels that’ll keep you on your feet all day.

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Joan Oloff is a podiatrist and founder of her eponymous shoe brand. Footwear is a family business, starting with her grandfather’s shoe store in Williamsburg, Brooklyn, which dates back to 1920. Eventually, Oloff followed her father and uncles into the business, working in their stores before becoming a podiatrist and launching her own brand. Through her designs, Oloff creates footwear that is both fashionable and functional. 

When culling this list of the best boots with heels, I asked Oloff to share qualities that she would prioritize when looking for shoes. I also leaned on my own experience shopping for shoes (including boots) for my wide, flat feet. Additionally, I asked PureWow editors for their recommendations and combed through hundreds of customer reviews, selecting pairs that were deemed both stylish and comfortable.

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When it comes to shopping for boots with heels, there are tons of options. So, how can you determine what’s going to be supportive?

“One of the first things I recommend women do when searching for supportive shoes is what I call the ‘flex test,’” Oloff tells me. “Simply hold the back of the shoe in one hand and try to flex the front upwards. There should be inherent stability to the structure of the shoe. If you can fold the front all the way to the top of the shoe, it’s lacking the basic stability necessary to support the foot.”

As a podiatrist, Oloff advises modifying your shoes if you need additional support. That could mean swapping out insoles for something with more cushioning, or choosing shoes that will relieve pressure points. And when it comes to knee-high boots, she would prioritize stretch leathers that can accommodate a variety of widths. Oloff adds, “Make sure there is enough room in the toe box area. You should always be able to wiggle your toes inside the boot. At the same time, make sure your foot doesn’t slide too far forward. Ironically, boots that are too big can make the boot feel too tight! Make sure there is enough flexibility in the leather so your foot can still bend at the ankle.” She also suggests choosing a breathable, natural fabric, noting that synthetics can cause more perspiration that leads to blisters, athlete’s foot and allergic reactions.