The 18 Most Comfortable Boots, According to Friends, Coworkers, and the Internet

While comfort has always been important when shopping for shoes, it's risen to the very top of our priority list when considering any new pairs right now. Whether it's flats, sandals, or as we'll dive into today, boots, there's no reason why our shoes shouldn't feel just as good as they look. And with fall fashion on the brain, I know there must be other people who, like me, are on the hunt for the most comfortable boots to wear all season.

With that in mind, I reached out to friends, family, and coworkers to see which boots they recommend, then also spent a good amount of time scrolling through sites like NordstromAmazon, and Shopbop for the most comfortable boots that have the best reviews with comfort specifically mentioned throughout. The results are in and it comes down to the following eighteen can’t-go-wrong options at every style, heel height, and budget. To see them all for yourself and shop along the way, just keep scrolling.

Dr. Martens have earned a reputation as being one of the most comfortable boots on Earth and based my own experience with these platform combat boots, I'm inclined to agree. Once you get past the break-in period, these feel like you're walking on clouds all day.

My sister adores these flat knee-high boots which have endured throughout Boston's harsh winters.

most comfortable ankle boots



"These By Far boots are the greatest," senior editor Allyson Payer says. "The heel is the perfect height and I love that you can wear them with even skinny jeans. I've walked for miles in them with nary a blister."

Payer also tells me that she's a big fan of these lug-sole boots. "I'm tempted to start wearing them now with dresses for a cool British-girl-at-Glastonbury look (Google Alexa Chung at Glastonbury for context)."

Editor in chief Kat Collings says, "these Tibi boots are the world's most comfortable boots. I'm pretty sure I could run a 5k in them. The height of the heel is perfect for a boost, but isn't so high that they're any less comfortable than flat boots. The chunky heel also helps with stability and comfort. And this, of course, doesn't add to the comfy factor, but that hardware on the back is such a special touch. I love the idea of it peeping out from the hemline of a skirt or a cropped pair of jeans."

Nordstorm customers pointed out how comfortable and cool these boots are, but I'd like to point out that they're from an It brand and currently 60% off.

I'm a big fan of these sleek Chelsea boots and, according to reviews, so are Nordstrom shoppers.

Scores of Amazon shoppers were compelled to give these fives stars for comfort.

Audience engagement editor Jasmine Fox-Suliaman says, "When I tell you these are the most comfortable boots I've ever owned—I'm not lying fam. I was searching non-stop for a cowboy boot last fall that I didn't hate and that would be comfortable enough to wear around the city, but seamlessly match various things in my wardrobe and low and behold these boots did it for me; I wore them just about everywhere, and they added an extra oomph to everything."

"So I don't own this exact style—yet," senior market editor Nicole Eshaghpour says, "but I have several pairs of shoes and boots from Paige and they all have the same cushioned insoles that make them more comfortable than any other brand of shoes I own. I'm always recommending their boots to anyone who needs something they can actually wear all day and/or night."

"If you want a comfortable ankle boot, I love, love, love this version from Schutz," insists Fox-Suliaman. "I originally bought the zebra version of this ankle boot from Nordstrom as an impulse buy—and honestly, it was the best money I ever spent. I wore these bad boys all over Spain (pre-COVID) and pretty much every day running around NYC. They're a great height to get the feeling of a heeled ankle boot, without the pain."

My friend Becca has lived in (and walked all over) NYC for the past six years and says these are one of the only shoes that have held up. Do with that information what you will.

Senior market editor Bobby Schuessler notes, "I wore these Chelsea boots all winter, and they've held up so well. I can't wait to wear them again come fall. I love the on-trend yet classic nature, and they're so comfortable with the extra light sole."

Shopbop customer Nikki says, "The color, fit, and style on these are amazing. I wear them a few times a week now because they're comfortable and go with everything. Only took a couple of days to break in and then they were perfect. I own almost 10 pairs of Frye boots at this point and I haven't regretted a single purchase."

"More than any other boots in my closet, I wear knee-high kitten heels on repeat," senior editor Kristen Nichols tells me. "Whether styled with a long dress or with a pair of trousers tucked inside, they pair perfectly with all of my fall staples. The low kitten heel makes them much more comfortable to walk in than my boots with taller heels. This style from Neil J. Rodgers are super soft, slightly slouchy, and I can't wait to start wearing them again next month."

These caught my eye because they align with a major fall 2020 boot trend, leather over-the-knee boots, but Shopbop customers rave about how comfortable and well-fitting they are on the calf.

Fox-Suliaman says, "If you're looking for a comfortable heeled knee-high boot, I highly recommend LPA's, Greta Boot. While I have the black crocodile version, I swear by the comfort of these boots and if you don't believe me just know that pre-COVID, I wore these in New York City hopping on and off the train; so yes, they're comfortable. And for an added bonus, they just make you feel fabulous."

It doesn't get any more classic than these leather knee-high boots and to further convince me, Shopbop customer Alice says that the heel on them is a good height for walking and that the leather is stiff enough so the shaft will stay up.