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Whether you’re in need of a classic ankle boot or looking for an all-weather winter boot to combat the oncoming chill, there’s no denying that boot season has arrived. This wardrobe staple is a fall and winter essential, so it’s not a surprise that there are boots of all types out there for any occasion. But when it comes to finding the most comfortable boots, it can feel nearly impossible.
That’s because most of the boots out there aren’t constructed for comfort. And in fact, some of the styles that caught my eye actively make my feet ache just looking at them (sorry, pointy toe and heeled boots!). But via trial and error, I’ve learned that doesn’t have to be the case. After years of putting them to the test, I'm finally ready to share my very own favorite pairs of the most comfortable boots that have withstood long hours on my feet, wintery dog walks, and daily commuter life. (Spoiler: one of them is even under $40!). So, if your aching feet are in need of a new pair this season, I’ve got you. With proper support, materials, and insoles, boots can be pain-free.
Meet the Experts: Priya Parthasarathy, D.P.M., a podiatrist based in Silver Spring, MD; Paul Langer, D.P.M., a sports medicine podiatrist based in Minneapolis; Chris Mohr, R.D., Fitness and Nutrition Advisor.
To help organize the nearly infinite boot options out there, I sat down with podiatrists to hear the criteria for what makes a comfortable boot, what brands they recommend, as well as pored through hundreds of reviews—and my fellow editors’ own closets and personal faves—to bring you the most comfortable boots to shop this season for every foot type (including wide feet and wide calves!), occasion, and aesthetic—all under $200.
1
Overall Most Comfortable Boots
Dr. Scholl’s Rate Ankle Bootie
Pros
- Roomy toe box
- Available in wide widths
- Easy-to-pull on tab and zipper
- Podiatrist-approved insole
Cons
- Mixed reviews about shoe sizing
These podiatrist-recommended boots have already been featured on our round up of best shoes for plantar fasciitis for their cushioned insole that’s designed to support foot health. Reviewers rave that these are the most comfortable boots for walking long distances due to its roomy toe box and microfiber fabric that helps with ventilation—not to mention they look pretty chic, too.
What a reviewer says: “Great bootie with barely-there heel. Sole is not slippery on floors. Zipper on side helps get the shoe on when open and ankle space is snug when zipper is closed so shoe isn’t flopping around the ankle. True to size. Rounded toe box. I’m buying additional colors since the fit is so good. Also has insole cushioning for extra comfort.”
Sizes | 6-13W |
---|---|
Colors | 8 |
Fabric | Microfiber suede |
Pros
- Anti-slip sole
- Easy on-off side zipper
- Water-resistant
- Comfortable knit ankle collar
Cons
- Less durable than real leather
This pair is a personal favorite—and is by far the most comfortable boots in my wardrobe. I purchased them four years ago and have been shocked by how durable they have been for their paltry $35 price (similar styles go for upwards of $150 for comparison’s sake). No, they’re not made from real leather, but that actually helps make them more comfortable, since it requires zero breaking in. The material is water resistant—perfect for rain or snow, and the knit ankle collar makes them extra cozy. The outsole is thick and grippy, and the insole is just cushioned enough to withstand pounding the pavement of my commute all fall and winter long. My favorite feature though? The gorgeous laces are great for customizing the fit, but its side zipper makes it a breeze to take on and off.
What a reviewer says: “I love the look of these boots. They’re just perfect. I wore them a few minutes at home, then took them with me on an eight day trip as the ONLY footwear, and they were SO comfortable. Do I wish they were natural leather? Yes, but then they wouldn’t be this price. I did get some wear and tear on my trip, but that only served to make them look more ‘authentic.’ I think they’re a great pair of boots. Also, the inner side zip is EVERYTHING.”
Sizes | 5-11 |
---|---|
Colors | 3 |
Fabric | Polyurethane |
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3
Most Comfortable Lug-Sole Boot
Steve Madden Howler Fashion Boot
Pros
- Soft suede fabric
- Non-slip sole
- Fashion-forward
Cons
- Some reviewers complain they run small
All fall fashionistas know that a lug-sole Chelsea boot should be a staple in everyone’s wardrobe. The versatile style goes with dresses, jeans, and even athleisure. This ultra-soft pair from Steve Madden has over 2,000 Amazon fans raving about their comfort and ease of wear. That might have to do with its suede fabric, easy-on pull tab, and non-slip outersole. It’s also available in a wide range of colors for every aesthetic.
What a reviewer says: “Fits perfect! Very well made and comfortable. I have gotten tons of compliments. There was no breaking in period. I wore the all day at work and did not have sore feet.”
Sizes | 5.5-11W |
---|---|
Colors | 12 |
Fabric | Suede leather |
4
Most Comfortable All-Weather Boots
Skechers Marlie-Weekend Chat Ankle Boot
Now 12% Off
Pros
- Podiatrist-developed removable insole
- Good arch support
- Water- and stain-resistant
- Roomy toe-box
Cons
- Some reviewers complain of mixed sizing
This cold-weather knit collared pair of water-resistant booties has extra mid-sole cushion for arch support that is podiatrist-approved. More than just approval, Skechers’ Arch Fit technology was actually developed by podiatrists to help distribute foot pressure to eliminate pain before it starts. The removable insole is also machine washable and will adapt to your own stride, making it a more comfortable boot the longer you walk.
What a reviewer says: “The first day I wore these for any length of time, I walked nine miles in New York City. My feet were the only part of my body that didn’t hurt! I just bought in another color. Get theses. You won’t regret it!”
Sizes | 5-12 |
---|---|
Colors | 3 |
Fabric | Vegan leather |
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Pros
- Built-in insole for arch and heel support
- Durable leather fabric
- Side zipper for easy on-off
Cons
- Pricey
Tall boots might be a fashion staple, but they can be bulky, cumbersome and downright uncomfortable to wear. But not this pair—these tall boots feature built-in orthotics for optimal heel and arch support to help relieve foot pain and fatigue. A memory foam mid layer ensures responsive cushioning and shock absorption. Made from premium leather, they’ll be long-lasting, too.
What a reviewer says: “I needed a new pair of boots, and I love ABEO shoes. I was so glad to find these which have a simple style and a good price. They are also very comfortable.”
Sizes | 5-11 |
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Colors | 2 |
Fabric | Leather |
6
Most Comfortable Boots for Plantar Fasciitis
Kuru FLEX Astra
Now 10% Off
Podiatrists everywhere recommend shoe brand Kuru for its superior support. This bootie features the same cushioned insole, midsole arch support, and flexible outer as the brand’s podiatrist-approved sneakers. And it’s cushy heel and rocker heel make it ideal for those struggling with heel pain and plantar fasciitis.
What a reviewer says: “These boots are so comfortable—as comfortable as sneakers—but look really nice. My feet felt good in them immediately. Can’t wait to wear them all winter long!”
Sizes | 6-11 |
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Colors | 2 |
Fabric | Leather |
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Pros
- Shearling lining for extra warmth and cushion
- Quality fabrics are durable
- Good for wide feet
Cons
- Some reviewers complained of difficulty taking them on-off
They might not be ideal for walking long distances, but there’s no denying the comfort of these Classic Mini Uggs. Lined with an ultra-soft shearling to keep your toes warm through even the coldest days of winter, they’re crafted with quality fabrics that will last season after season. Though some might say they’re back in-trend this season, I don’t think they ever left. They’re my forever go-to for winter dog walks for their durability and extra soft comfort. There’s a reason they never go on sale.
What a reviewer says: “These boots are my favorite daily shoes in the winter. I did use waterproof spray on them ahead of time, which seems to be working to keep these in good shape. Super cute, warm, and comfortable.”
Sizes | 5-12 |
---|---|
Colors | 19 |
Fabric | Suede leather |
Pros
- Comfortable memory foam insole
- Non-slip sole
- Soft suede fabric
Cons
- Runs big
Via a combination of its flexible outersole, low heel, and plushly cushioned memory foam insole, this pair from Clarks is in the running for the most comfortable boots out there. Made from real suede and featuring a stylish ankle strap, they are just as chic as they are comfortable, too.
What a reviewer says: “Clarks were on the list of shoes my podiatrist gave me to help with my plantar fasciitis. I wear these with an insert, and I can walk all day without pain. I also look fashionable while doing so! They’re so cute! And they run true to size.”
Sizes | 5-11W |
---|---|
Colors | 3 |
Fabric | Suede leather |
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Pros
- Long-lasting leather
- Regular and wide-calf sizes available
- Low heel
Cons
- Lacks arch support
“These are hands-down the most comfortable boots I’ve ever worn,” Hearst’s associate editor, Lauren Gruber says of her favorite western boots. “I’ve stood and danced in them for over eight hours at a music festival without my feet getting tired. The mid-calf height is super versatile and I’ve worn them with everything from casual jeans to dresses. I’ve had them for over three years and they still look as good as new, thanks to their durable, scratch-resistant leather material. Plus, they come in standard and wide calf sizes!”
What a reviewer says: “They are beautiful boots and the wide calf is amazing! At varying weights, I’ve always had wide calves—currently prob 18-18.5” circumference. These fit great on me up and around jeans with even some extra room so it doesn’t look like sausage casing on my legs. So glad wrist extended their sizing! Can’t wait to wear these out!”
Sizes | 5-12W, wide-calf |
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Colors | 2 |
Fabric | Leather |
Pros
- Great arch support
- Comfortable and durable leather build
- Platform front makes heel drop lower
Cons
- Pricey
If a comfortable heeled boot has been your fall-wardrobe white whale, look no further than this pair from Vionic. The brand is known for their cushioned orthotic insoles with contoured arch support and a deep heel cut for extra stability, which makes walking in heels a lot more comfortable. While this may look like a hefty heel, the front platform helps lower the heel drop to a measly inch for a more comfortable stride without being clunky.
What a reviewer says: “I love my black leather boots, great to dress up for work professional and great to dress down for casual look. I wish they would come in tan, too. Great arch support!”
Sizes | 5-12W |
---|---|
Colors | 3 |
Fabric | Nubuck leather |
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11
Most Comfortable Hiking Boots
Hoka Anacapa 2 Mid GTX®
Pros
- Lightweight
- APMA Seal of Approval
- Waterproof fabric
Cons
- Some reviewers complain they run narrow
In terms of shoes that need extra comfort, hiking boots are at the top of the list. If you’ve been burned by blisters and tense ankles after a long climb, this pair from Hoka will feel like a dream in comparison. They boast an American Podiatric Medical Association (APMA) Seal of Acceptance for promoting good foot health, most likely due to its ergonomic cushioned foot bed, lightweight body, and grippy Vibram non-slip sole, which make it easy to wear for hours at a time.
What a reviewer says: “I bought these and took them out for a quick two mile jaunt. They were comfortable right out of the box and I appreciate the fact that they’re lightweight and sturdy at the same time. I trudged through mud with no slipping. I splashed through pretty deep puddles and watched with glee as the water rolled right off that Gore-Tex. I clambered up rotten logs to peek down at a mossy ravine. I walked down a rocky path to spy on basking turtles with no ankle rolling. The entire time I was out there, I didn’t worry about my feet once.”
Sizes | 5-11 |
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Colors | 5 |
Fabric | Nubuck leather, recycled materials |
How to choose the most comfortable boots
Go for a rounded, wide toe box. If you’re more drawn to pointy or pinched toe styles, chances are they’re not going to be all that comfy. This kind of style can “lead to blisters and calluses from more friction and pressure. More serious problems like overpronation, underpronation, or plantar fasciitis can happen as the foot compensates for improper alignment or support.” Chris Mohr, R.D., Fitness and Nutrition Advisor says. So, when you try on your (rounded toe) boot, make sure you can spread your toes out.
Look for a lower heel. “The higher the heel, the more stress is placed on the knees, hips, back, and forefoot,” says Paul Langer, D.P.M., a sports medicine podiatrist based in Minneapolis told Prevention. If walkability is of importance, podiatrists recommend wearing boots with less than a two-inch heel.
Pay attention to the insole. When it comes to maximizing foot comfort, it’s ideal to have a cushioned insole with arch support and a deep heel cut. This ergonomic shape will help stabilize your foot and ankle, and add to overall comfort levels. That’s why it’s great to opt for a boot from a podiatrist-approved brand like Vionic, Hoka, or Skechers, whose insoles hit all those marks. If that’s not possible, Priya Parthasarathy, D.P.M., a podiatrist based in Silver Spring, MD recommends looking for a boot with “a removable insole allows you to use custom orthotics or more supportive insoles if needed.”
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How we chose the most comfortable boots
We consulted our editors for their own recommendations, received expert advice from professional podiatrists, and pored through thousands of reviews to bring you the most comfortable boots for every weather condition, foot type, style, and budget.
Why trust us
For more than 70 years, Prevention has been a leading provider of trustworthy health information, empowering readers with practical strategies to improve their physical, mental, and emotional well-being. Our editors interview medical experts to help guide our health-focused product selections. Additionally, Prevention also examines hundreds of reviews—and often conducts personal testing done by our staff—to help you make informed decisions.
Charlotte Lewis
Senior Commerce Editor
Charlotte Lewis is the Senior Commerce Editor at Prevention. After a decade of working in Hollywood writers’ rooms and contributing pop culture writing to ETOnline, Bustle, TVGuide, and CBS, she underwent bariatric surgery and changed her focus to health and wellness. Previously, Charlotte was the Sexual Health & Wellness Writer for Refinery 29. There, she wrote and edited shopping content about new wellness trends, beauty launches, and sex-positive products. She currently lives in Brooklyn with her girlfriend—and the love of her life, her senior dog, Rory. All three can typically be found perusing the Fort Green farmer’s market for fresh produce or curling up on the couch to watch Survivor.