The 17 comfiest ankle boots for women, according to podiatrists | CNN Underscored (2024)

• Related: The 27 best fall fashion essentials under $100 at Nordstrom, according to fashion experts

• Related: Men’s fall fashion essentials: A head-to-toe guide

1. Proper Fit: The most crucial factor in selecting comfortable ankle boots is ensuring they fit properly. Make sure to measure both feet and choose the size that accommodates the larger foot (and don’t forget about width).
2. Arch Support: This is essential for overall foot comfort and alignment. It can also prevent fatigue and discomfort, especially if you’re planning to wear the boots for extended periods.
3. Padding: Adequate cushioning is vital for reducing impact and providing a plush feel as you walk. Look for boots that have cushioned insoles, padded collars, and possibly even memory foam inserts.
4. Heel height and shape: If you’re looking for all-day comfort, opt for a lower heel (less than 2 inches) or even a chunky block heel that offers more stability.
5. Ankle Support: Make sure the boots provide adequate support around the ankle without causing any rubbing or discomfort. Examples of ankle support are an elastic or lacing system to dial in the desired tightness.
6. Toe Box Space: A roomy toe box, where you can easily wiggle your toes, is essential for preventing cramped toes and ensuring a comfortable fit.

You can wear these sleek Sorel boots as your everyday fall shoes or as your go-to rainboots, thanks to the waterproof leather or suede. This ankle boot has a 1.25-inch block heel as well as elastic sides. “It also features a heavy-duty rubber sole that can be worn in any type of weather,” Oldani says.

These stylish-meets-professional oxford booties come in a range of neutral colors with a 1.5-inch heel. But according to Daughtry, that’s not the best part. It’s the removable footbed that gives you “the ability to add orthotics but also offers Naot’s anatomic cork-and-latex footbed that molds to your foot structure,” she says. Plus, they also have a lightweight yet abrasive metal shank to avoid slipping. “Rugged outsoles that have a low heel make for the ability to navigate various weather conditions easier and [make you] less likely to fall in unpredictable cold and wet weather,” adds Daughtry.

One of the most important things to look for, according to Dr. Tim Oldani, is a toe box like the one on these Vionic boots, which is rounded (aka wider) versus narrow or tapered. “This is especially important for those with forefoot deformities, such as bunions, hammertoes or neuromas,” he says. This Chelsea-style ankle boot has a 1.5-inch heel and elastic sides. “It also has Vionic’s EVA removable footbed, which was originally designed for those dealing with plantar fasciitis,” he adds.

If you’re going to be spending a lot of time on your feet but still want to look chic, Daughtry recommends checking out one of Naot’s best sellers: the Helm bootie. “There’s a huge variety of colors,” she says, with all water-resistant leather or mixed leather and suede uppers and padded lining. “The removable footbed makes it orthotic-friendly, but it also features Naot’s anatomic cork,” she adds, “and the latex footbed is wrapped in microfiber and leather, which molds to the shape of the foot.”

When it comes to boots you’ll want to wear all season, Tran explains that proper fit is paramount. “This is a boot that checks off all the boxes,” Tran says. “There is a wide toe box, minimal heel height, lots of cushioning, and [it] can be paired to create a trendy look.”

This waterproof suede, hidden-wedge ankle boot smartly designed by Sorel is perfect for anyone running around all day who doesn’t want to compromise style for comfort. “The Chelsea design with a finger loop on the hind heel makes it easy to slip or off, and the rubber soles are durable and good for light agility,” Dr. Yolanda Ragland says. “A pair of ankle boots with cushioned insoles or contoured footbeds will provide good arch support and can prevent discomfort and fatigue during extended wear.”

With a flexible sole, natural cork insole and vegan water-repellent leather, the Patrol Lite Boot was designed to support your natural gait. “Feelgrounds is one of the barefoot brands that make shoes that keep your foot health in mind but are also stylish,” Dr. Sondema N. Tarr says. “Minimalist footwear has many benefits, including strengthening your feet and legs over time, improving foot flexibility and increasing your sensation with the ground beneath you.”

“If you want a good ankle boot that’s durable and will last you a long time, Dr. Martens Unisex Boot is a great option,” Dr. Janine Ferrigno-Taddeo says. “Its classic appearance never goes out of style, and its durability makes it great for long walking trips or everyday wear.”

Daughtry vouches for these waterproof leather ankle boots with the “perfect” 2-inch heel height with an easy side-zip entry and the ability to add arch supports. “Overall, it is best to have a stable, all-weather or water-resistant outer material that has components that make putting on the boot easy and comfortable while also being stylish,” she says.

These leather ankle boots aren’t just waterproof; they also have built-in orthotic arch support for added comfort. “Vionic is well known to be one of the few shoemakers that makes dress shoes and sandals with arch support,” Tran says. “This Chelsea-style boot is no different—an awesome look with plenty of support.”

For crisp or rainy fall days, you can’t go wrong with the original L.L.Bean boot in 6- or 8-inch height. “Handmade in Maine, this is a classic all-weather outdoor boot with grippy soles, sturdy stitching, weatherproof leather, and extra room for thick socks,” Daughtry says.

Birkenstocks don’t just shine when it comes to supportive sandals. “Birkenstock is historically known for functionally comfortable footwear, with footbed designs with deep heel cups, transverse and longitudinal arch support, toe grip and their signature footbed edge,” Ragland says. “I was drawn to these trotters because I absolutely love the cork wedge heel — cork is arguably the best natural material for soles due to how effective it is with shock absorption.”

Available in three colors, this water-resistant suede bootie has a built-in orthotic system to help with arch pain and heel pain, according to the brand. “It features a removable insole with proper arch support to help align your body from the ground up,” Ferrigno-Taddeo says, “and the insole also has UltraSky cushioning to provide pressure relief and extra comfort, helping to reduce the pain associated with ailments like plantar fasciitis.”

The quilted detail gives these boots a cozy feel, but it’s the zipper accent with lace-up closure that makes these boots not only easy to put on but versatile. Daughtry suggests looking for boots like these with the “ability to accommodate for thicker socks … This can assist with keeping feet warm and comfortable.” If that’s not enough, she notes that these boots are American Podiatric Medical Association (APMA) Accepted for promoting good foot health and are “orthotic-friendly but also [offer] Naot’s anatomic cork-and-latex footbed, which molds to foot structure.”

Ragland describes Tamara Mellon as the ultimate luxury shoemaker (or Shoe Fairy) and says that the Perfecto, perfectly named, is an ankle boot you will not regret splurging on. “The inner zipper allows for easy accessibility, and the outer buckles add adjustability for ankle support,” she says. “The full thickness of the leather is why the boot is so durable, yet it’s supple enough for prolonged wear. I trudge around in these all over New York City from car to subway to bike-shares effortlessly. My feet feel cozy and comfortable due to the cushioned insole and thick, grippy rubber outer sole.”

Although these boots hit slightly above the ankle, Tarr vouches for them as one of the best in the category. “They have high-quality materials and construction, a deeper toe box for people with foot deformities like hammertoes, and this shoe also comes in a wide,” she says.

Daughtry also recommends these unisex water-resistant leather boots with pull tabs for easily slipping on and off as well as shock-absorbing outsoles. “They’re great for all-day walking, as they’re very cushioned and absorb 90% of impact while walking,” Daughtry says. Plus, they also have a removable footbed, making them orthotic-friendly.