These Cute and Comfortable Ankle Boots Are Perfect for Fall and Winter

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Is there any wardrobe staple quite so versatile (and hard to find) as a quality pair of booties? We practically live in the things from September to May—but finding the most comfortable ankle boots can feel nearly impossible, especially with so many options.

As we inch our way into sweater weather, ankle boots are practically a must-have for every outfit for every occasion, no matter if you’re returning to the office, heading out for a much-needed date night, or going on a adventure to find the peak foliage colors. But not all boots will fit your needs (and feet) the same way. No need to stress: whether you are on the hunt for great arch support options, trendy styles, or waterproof materials to hold up against any winter weather, we’ve got you covered.

Meet the Experts: Jay Bhuta, D.P.M., a podiatric surgical expert at Ankle & Foot Doctors of New Jersey, Paul Langer, D.P.M., a sports medicine podiatrist based in Minneapolis, Saylee Tulpule, D.P.M., a podiatrist with Foot and Ankle Specialists of the Mid-Atlantic in Maryland.

To keep you on the move, we asked podiatrists for their best ankle boot recommendations (with maximum comfort in mind) and combed through thousands of online reviews—and we found the pairs (all under $300!) that are worth the investment.

Our top picks

Ready to strut your stuff in super comfortable kicks? Shop our favorite ankle boot picks below:

558 Boots

A favorite of everyone from ranchers to city slickers, these time-honored boots are cute enough to post online, but durable enough to survive rain, snow, and yard work. Better yet, they boast shock-absorbing outsoles and removable footbeds, meaning you can add your own orthotics. Saylee Tulpule, D.P.M., a podiatrist with Foot and Ankle Specialists of the Mid-Atlantic in Maryland,
likes them for their “cushion, pulls tabs for easy slip-on, and casual feel,” mentioning that they’re great for all-day walking. At just under $200, they’re certainly an investment, but one that you can trust will survive many colder seasons to come. One Zappos customer writes “My first pair of Blundstones lasted 10 years. I imagine these will last that long, too.”

Rate Ankle Boot

These perforated suede ankle boots look at least double their price, and they come loaded with the brand’s signature cushioning and a pull tab for easy wear. Plus, reviewers love how easy they are to style with cold-weather outfits. “The insole is amazing, it forms to your feet which feels great and makes it so there’s really no break in time for them and were comfortable from the jump!,” one reviewer says. They even come in wide sizes, although wearers warn that they are narrower than one might expect.

Kamryn Boots

Whether you’re hitting a meeting or happy hour, these sleek, understated ankle boots are exactly what you need to complete your look. Beyond their aesthetics, though, there’s plenty else to love, including a 1.59-inch heel, hidden arch support, and a removable footbed, which are great for all-day wear, Dr. Tulpule notes. You can choose among four colorways, but classic black is always a safe (and chic) option. One Zappos reviewer says “these are my go-to footwear if I was going to do a lot of walking and did not want to have any foot problems.”

Neko

Dr. Tulpule herself has issues with plantar fasciitis, and she says these boots get her through fall and winter with zero issues, thanks to their removable insoles, short-but-stylish heels, and zip closures. For extra support, slip in your own orthotics—you’ll actually be able to walk around comfortably. One happy Zappos customer adds that “Munro has a generous toe box, so your toes won’t feel pinched.”

Midform Chelsea Platform Leather Boots

Featuring side stretch detailing and a finger loop at the ankle, these are some of the easiest boots to slip and keep on. “I would highly recommend these for patients with bunions,” Dr. Tulpule says, because of their wide toe box and a design that easily accommodates custom orthotics. Plus, they’re waterproof and plenty cushioned—not to mention modern and stylish, too. One Amazon customer says “Loved these boots, so comfy that I ordered in another color!!!”

The Rain Boot

Everlane’s classic boots are both functional and stylish, and affordable at that. Chelsea-style stretch panels on the sides make them easy to slip into, while slip-resistant outsoles keep your feet firmly planted, even during downpours. And their wide, rounded toe box also allows ample room to wear comfy socks. Jay Bhuta, D.P.M., a podiatric surgical expert at Ankle & Foot Doctors of New Jersey, especially likes these boots for people with wide ankles, since they have plenty of room at the top. One Everlane reviewer points out how she loves “the thickness of the sole and rubber. It really feels substantial, like it’ll hold up against nasty weather!”

Bean Boots

You’ve probably owned a pair of these at some point, and for good reason: They’re a classic with some impressive specs. Built with grippy soles, sturdy stitching, and weatherproof leather, they’re ideal for those gray days that start around October. “They’re perfect for those cold, wintry months,” Dr. Tulpule says, and they even come with extra room for warm socks. One happy Zappos reviewer writes “I was extremely happy as the fit was perfect and they are extremely comfortable to wear all day long (even at my job where I am on my feet for 6+ hours).”

X Ultra 4 Mid GTX

These hiking boots have a high-tech charm to them—they’ll look great on the trail and on city streets alike. Dr. Tulpule especially appreciates the fact that they’re waterproof, thanks to a trusty GORE-TEX outer, meaning they’ll survive the slush in your future. And on top of all that, their rugged outsoles are designed to make tough descents as safe as possible. Bonus? These are orthotic friendly! One Zappos customer says “Even with my orthotics, they still fit great and allowed room for my toes to spread in the toe box.”

Laurel Ankle Bootie Boot

This new-school take on the classic Chelsea boot is just begging to be worn this fall. Available in an assortment of leather and suede neutral colors (all featuring a stacked, contrasting heel), they’re guaranteed to be in constant rotation. Dr. Tulpule appreciates the super-stable 2-inch heel, which is just high enough to make a statement, but not too high to be comfy, and Dr. Bhuta notes that the side stretch makes it easy to slip insoles in. One Amazon customer says “You can wear these walking around like a comfortable tennis shoe they are so comfy!”

6" Classic Moc Boots

When you can’t compromise performance (or style), Red Wings should be your go-tos. First introduced in 1952, this style has since been updated with soft, water-resistant leather, lightweight outsoles, and cushy insoles. Your boots can even be resoled, meaning they’ll last as long as you’re willing to keep them. The only drawback, reviewers say, is that they take a while to break in. Sure, they’re an investment, but one that you can trust. One Zappos customer says “These are the best and most comfortable work boots ever!”

Caribou Snow Boots

Whether you’re trudging through snow or going on a hilly hike, these Sorel snow boots will survive all of your winter adventures. The felt inner boot keeps your tootsies feeling toasty, while a vulcanized rubber shell ensures that water and slush stay out. Plus, that treaded, non-slip sole is the real deal, preventing slipping and sliding. Dr. Bhuta also points out the high laces, which help ward off twisted ankles and falls. One satisfied Zappos customer writes “They are warm and comfy and dry even with feet that perspire a lot.”

Felicity Marissa Suede Short Boot

These Western-inspired ankle booties are both right on trend and ideal for those with bunions, Dr. Tulpule explains, due to their ample room in the forefront. Like many other options here, the footbed is removable—but they stand out with the extra-durable leather croc heel, a slightly daring silhouette, and wide sizing. One Amazon reviewer writes “from the day I put these boots on, they were comfortable. I wore them non-stop for an entire 4-week trip!”

Charlene Ginger Nubuck Ankle Boot

So many wedges tower far above a comfortable heel height, but this pair from beloved clog brand Dansko clocks in at an easy-to-wear 1.5 inches. Available in black and burgundy, they’re subtler than other wedge options and, as a bonus, are also waterproof. One Amazon says she “could comfortably wear these all day long.”

Cordia Boots

“These boots provide more stability with laces, come in different widths to accommodate for bunions or wider feet, and are slip-resistant for wet conditions,” Dr. Bhuta says, making them a great lace-up choice for everyday wear. And besides being cute, those laces actually team up with the side zippers to prevent ankle injuries—a must for long walks. One Zappos customer says “These are the most comfortable boots I’ve ever worn. I found them by Googling ‘butter-soft leather boots,’ and they lived up to that description.”

Mazin Cayto Boots

With a 1-inch heel, a cushy footbed, and sturdy leather, these kicks fit all the criteria of a solid pair of walking boots. Reviewers report that they look just as good at PTA meetings as they do at the office or at drinks with the girls, and it’s a cinch to insert your own orthotics. Never thought you’d wear Hush Puppies? Give these comfortable ankle boots a spin first. One Amazon reviewer says “They needed no breaking in. Put them on and wore them all day!”

How to shop for comfortable ankle boots

✔️ Look for a low 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. If you’re planning on comfort and walkability, your heel should be no more than two inches tall, explains Dr. Tulpule, “so there’s no stress placed on the ball of the foot or the Achilles tendon.”

✔️ Avoid narrow or pointed toes. It’s not rocket science: Jamming your toes into a tiny point just won’t feel good after very long. “Look for width to ensure space for the forefoot,” Dr. Tulpule says, “especially for people with bunions.” Instead, look for pairs with a wide, rounded toe box; this gives your feet room to breathe and allows them to move more easily.

✔️ Pay attention to materials. Boots with zippers, straps, and other closures can help people who have difficult-to-fit feet, Dr. Langer says, and high-quality leather is among the most comfortable and pliable materials. Dr. Tulpule also recommends picking options that can survive the elements. Internally, she says that ankle boots should offer plenty of cushion and shock absorption, just like any other walking shoes. Alternatively, you can try adding orthotics, especially if the boots have removable insoles.

How we chose the best comfortable ankle boots

We consulted podiatrist experts Dr. Bhuta, Dr. Langer, and Dr. Tulpule, as well as considered thousands of online reviews to ensure that we picked the best comfortable ankle boots for every style and need.

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.

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