Comfortable ankle boots are the cornerstone of our fall and winter wardrobes. (And a pretty important part of our spring and summer outfits, to be honest.) But more than just being comfy, we want booties that look cute and happen to be good for our feet, too. Style, support and a reasonable price tag may seem like an impossible trio, so we asked three podiatrists for their expert advice on comfortable ankle boots. Here’s what they had to say on the matter, including 10 ankle boot styles that will kick off your most stylish autumn yet.

RELATED: We Had a Podiatrist Rank the Most Foot-Friendly Fall Shoes—Here are Her Top 5 (and One to Avoid at All Costs)

First, what should we look for when shopping for booties?

All three podiatrists recommend trying on new shoes at the end of the day when your feet are most swollen. “If they feel comfortable at the end of the day, most likely they will feel comfortable throughout the day,” says Dr. Miguel Cunha, a board-certified podiatric surgeon and founder of Gotham Footcare in NYC. Another handy trick to ensure your booties are the correct size? “Wiggle your toes,” Dr. Cunha suggests. “If you can’t move your toes at all then the boots are too tight and will eventually become painful.”

As you might imagine, the materials used to create your ankle boots matters, too. “The number one [thing to pay attention to] is the shank of the shoe,” says Dr. Sarah Haller, DPM, of Essex Union Podiatry. “You want a boot where you cannot twist the sole in the middle.” Dr. Cunha suggests looking “for a boot designed with smooth, solid leather uppers that are not only highly durable but also flexible and comfortable.”

If you prefer a heel over flats, don’t fret, there are still a plethora of podiatrist-approved styles for you to wear. “For everyday boots, choose a chunkier heel or stacked style,” and stick to heels that are two inches or shorter, advises Dr. Jaqueline Sutera, DPM, a Vionic Innovation Lab member. Dr. Cunha is a fan of wedge styles for additional arch support and actually recommends avoiding boots like Chukka boots that are often entirely flat. Instead, opt for something with a 1-inch heel to take some of the pressure off your Achilles tendon. That said, Dr. Sutera says it’s best to avoid anything over 3-inches, especially if the heel is a stiletto. “These tend to encourage hammertoes, bunions, ingrown nails and pinched nerves.” Ouch. Now, onto the shoes you should buy.

1. Blondo Liam Waterpoof Bootie

Dr. Cunha is a fan of Blondo for the brand’s dedication to waterproof materials and generous toe boxes. The Liam style in particular “has a wide toe box, is supportive, durable and slip resistant and features a heel height under 1.5 inches.” Although we often think of waterproofing for rain, snow or winter boots, Dr. Cunha recommends seeking this feature out as often as possible to help prevent bacteria or fungi from growing in the shoe, or worse, on your feet. That said, breathability is important to keep in mind, as well. “Standing and walking for prolonged periods of time can lead to one’s feet getting hot and sweaty,” which may have the same effect as unwanted rainwater or melted snow seeping in.

From $59 at Amazon

2. Cole Haan Harrington Grand Buckle Bootie

Dr. Sutera like this chic gray bootie because of the cushioning throughout the footbed, not just at the toe or arch. The suede upper is breathable and flexible enough to conform to your foot while still providing ample support at the front and top. Multiple reviewers rave about how comfortable they are, even right out of the box. Per one happy customer, “These boots feel great on one’s feet! Heels are just right, wore them for eight hours straight and felt no discomfort.”

Buy it ($123)

3. Rag & Bone Rover Chelsea Boot

“I am a huge fan of Rag & Bone,” says Dr. Haller. “The boots are made with quality leathers and there are a lot of solid, stable heeled options.” Two specific podiatrist-approved features of the Rover Chelsea boot are the 1 ¾ -inch block heel and the pull-on design. “Zippers directly over bones are a no-no. They cause too much friction,” warn Dr. Haller. That’s becuse they can causee excess friction, leading to blisters, irritation or even cuts and scrapes. One thing to note: Some reviewers found these Chelsea boots to run a little small, so you might want to consider ordering a half-size up, especially if you’re often between sizes.

Buy it ($395)

4. Vionic Serena Ankle Boot

Vionic was actually founded by a podiatrist and focuses entirely on creating shoes that are both good for your feet and fashionable enough for everyday wear. The company has a rather impressive and varied celebrity following, including Oprah, Kristin Cavallari, Alexa Chung and Margot Robbie, among others. For fans of flat or low footwear, the heel on this easy Western bootie is just high enough to relieve pressure from your Achilles tendon without actually adding too much height. Plus, they’ll go with everything from your fave skinny jeans to your new quarantine-approved nap dress, and last for years to come.

Buy it ($160)

5. Børn Donella Chelsea Boot

Yes, the heel on these ankle boots looks high but it tops out at 3-inches—meaning it meets our experts' recommendations However, Børn’s first priority is to create shoes that are comfortable, easy to wear and it was named as one of Dr. Sutera’s go-to brands. To account for the higher heel, these booties come with a cushioned footbed that provides extra arch support and feature a steel shank to sturdy your feet. The higher shaft also helps stabilize your ankle as you walk.

Buy it ($165)

6. André Assous Lace-Up Boot

Combat boots are trending for 2020, but that doesn’t mean you need to stick to classic black Dr. Martens. This zebra-print pair come with a memory foam-cushioned insole that’s comfy enough to make your mattress jealous. They’re also waterproof and have an Achilles tendon-supporting 1 ½ -inch heel. The adjustable laces also give you the opportunity to tighten or loosen (aka, add or reduce support) as needed. PureWow’s very own fashion director, Dena Silver, says these feel like you’re walking around in a pair of cozy winter socks more than lug-sole boots.

Buy it ($198)

7. Everlane The Day Boot

One PureWow staffer swears these booties are as comfortable as her favorite sneakers and based on the number of 5-star reviews they’ve received, she’s not the only one who thinks so. Multiple people use the phrase “buttery soft” to describe the leather exterior and many admit to owning more than one color, with plans to snap up a third or fourth pair. Writes one happy customer, “I have ignored all my other block heel boots in my closet since purchasing these. They’re so sleek and modern and require no breaking in time, with no irritation…since the leather is buttery soft.” The only caveat appears to be slightly inconsistent sizing. Per the website, sizes 5 through 6.5 might run a little large, size 7 through 8.5 should fit true to size, and sizes 9 through 11 run a little small, so take that into consideration before you add to cart.

Buy it ($236)

8. Geox Calinda Bootie

The sole of these chic booties is entirely waterproof, while the leather upper is water repellant, so your feet will feel fresh all day long. Ample cushioning in the footbed helps balance out the 2 ½-inch heel, which has a wide base for plenty of support but a tapered detail at the top for a more trendy shape. You truly can’t go wrong with these Geox babies.

Buy it ($200)

9. Dr. Scholl’s Original Collection London Block-Heel Bootie

Dr. Scholl’s is another brand known for its dedication to addressing foot health. Of course, there are the insoles and blister treatment/prevention kits, but there are also the gorgeous shoe designs to consider, like these trendy snakeskin western ankle boots. They come in three colors (black-and-white snake, cheetah spots and classic black), each of which are accompanied by a lug sole that’s both practical and statement-making. There’s also the luxurious memory foam footbed that feels like walking on a cloud. These booties do tend to run small, so you might want to consider going half a size up from your usual.

Buy it ($75)

10. Marc Fisher Ltd Yale Chelsea Boot

Marc Fisher Ltd has long been one of our favorite shoe brands, though not every pair meets our podiatrists’ criteria. This 1 ½-inch block heel Chelsea boot, however, is chic and supportive, garnering our expert’s stamp of approval. It also comes in eight different colors, meaning there’s bound to be a pair that will fit seamlessly into your existing wardrobe. The stretchy goring on both sides makes pulling them on a cinch and eliminates Dr. Haller’s aforementioned zipper concerns. Per one 5-star reviewer, “Love these and have worn them almost daily for the last two years. They’re SO comfy and cute. Runs true to size but may seem tight at first but will stretch and mold to your feet.“

Buy it ($179)

RELATED: The 12 Most Comfortable Boots That Won’t Leave You With Blisters After Just One Wear

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