The 20 best ankle boots for women, according to stylists and podiatrists

One of the most important things to look for, according to Missouri-based podiatrist 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.

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 footbeds that give you “the ability to add orthotics but also offer Naot’s anatomic cork-and-latex footbeds that mold 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,” Daughtry adds.

New York City-based fashion stylist Audree Kate López raves about these pointed-toe ankle boots. "I love these boots because the skinny shaft is easy to tuck under pants; the suede, brown color and kitten heel hit the 2024 trend marks; and these can style easily with a dress or jeans," Lopéz says. Plus, they'll give you a bit of height — 2.75 inches, to be exact — while staying comfortable, thanks to MWL Cloudlift Lite padding.

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 removable footbeds, making them orthotic-friendly, and come in eight neutral colors.

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.

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 bestsellers: the Helm booties. “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, Dr. Nam Tran of Dallas Direct Podiatry 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.”

"I don’t think you have to buy a black or brown boot for it be versatile in your wardrobe. Personally, my silver metallic cowboy boots, leopard ankle boots and studded combat boots get a lot of wear, so as long as you like them, can wear them and they're an easy grab when getting dressed, go for it!" López says. The stylist adds that this burgundy hue will be a popular choice for fall and winter. "I love these boots because you get a subtle animal print with the tonal croc cap toe, and the pointed square toe is trendy but timeless."

These waterproof suede, hidden-wedge ankle boots smartly designed by Sorel are 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,” says Dr. Yolanda Ragland, CEO and founder of Fix Your Feet, Inc. “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 flexible soles, natural cork insoles and vegan water-repellent leather, the Patrol Lite Boots were 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,” says Arizona-based podiatrist Dr. Sondema N. Tarr. “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,” says Dr. Janine Ferrigno-Taddeo of Millburn Podiatry in New Jersey. “Its classic appearance never goes out of style, and its durability makes it great for long walking trips or everyday wear.” While the brand's classic 1460 ankle boots are notoriously painful to break in, they now come in an Ambassador leather that are soft and pliable straight out of the box.

“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.” Daughtry also 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.

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.”

For a statement-making pair, celebrity stylist and TV personality Cindy Conroy loves these faux-snakeskin boots from Steve Madden. "Beautifully cut, it’s the right balance of sculptural and functional," she says. "Available in size 5 through 12, I love how inclusive it is." They also come in Black Leather or Chestnut Suede, which are both equally as chic.

Available in three colors, these water-resistant suede booties have 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.”

These mini boots are a budget-friendly alternative to real-deal shearing booties, and they're even weatherproof. "Suede booties are a great idea until they get wet. But that’s what makes these so different," Conroy says. "They’re sealed with a splashproof coating so light rain and snow won’t ruin them. That TPR sole is also great for grip and traction."

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.”

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.

"Suited and booted, these delightful lace-up combat boots deliver on fall and winter practicality," Conroy says. "Made of PU leather, they’re chunky, playful and a little rebellious. But what I love most is the zip closure and the shaft height of the boot. Those extra inches of material will protect your ankles from blistering winds and piles of snow."