Ankle boots have established themselves as a wardrobe staple deserving high-end status right next to high boots. In fact, I find that I gravitate towards ankle boots as a more versatile and comfortable option than tall boots (I recommend Jo-Lynne Shane’s style primer on how to wear ankle boots if you’re still wondering). Have you ever found a stylish and comfortable pair of ankle boots? Those that rock your foot, fit you like a glove and go well with your wardrobe in cooler weather? With the thousands of ankle boots online and in stores, it is mind-boggling trying to decide which one will work for you and your particular foot issues. Let us help you narrow your search with our selection of 6 comfortable ankle boots for everything from plantar fasciitis to hallux rigidus. And if you still can’t find what you’re looking for, check out our lively discussion of comfy ankle boots on our Facebook page!
The most comfortable ankle boots for plantar fasciitis: Naot Helm. Take Zappos client Sharon:
I have suffered from painful plantar fasciitis for over 2 months; shots from a podiatrist; I donated multiple pairs of shoes and spent so much time looking for and returning every type of shoe I could wear (yes – and different supposedly orthopedic insoles). here are the The only ones which I was able to wear painlessly and walk normally instead of limping.
We love the Naot Helm’s ability to perfectly combine avant-garde aesthetics with orthopedic comfort. Find the Naot Helm in six beautiful colors, Euro sizes 35-43 (4-12) for $ 199.95 at Zappos. Check out our educator review on the darling Naot Kahika bootie for another comfy option with a rounded toe and a more “relaxed” look.
Best boot for hallux limitus or rigidus: Dansko Barbara.
If you have hallux rigidus (a big toe that hurts due to injury or arthritis), you’ve probably been told to wear a shoe with a firm sole to prevent the big toe from flexing too much. But sometimes stiff-soled shoes can be harsh and unforgiving on sore feet and toes. Thankfully, the Dansko Barbara doesn’t just feature a chunky (but lightweight) outsole with a rocking motion, the insole is generously padded with memory foam. The toe area is spacious to accommodate sensitive toes. Find the Dansko Barbara in 36-42 euros (5.5-11.5) for $ 170 on Dansko.com and Zappos.
The adorable Dansko Bettie is similar to the Barbara, but with a flip-up sheepskin collar! Find it on Dansko.com and Zappos.
Do not forget the Fitflop boots if you have a hallux limitus or rigidus. Most have thick, cushioned soles with roomy toecaps. The styles are getting cuter!
Best affordable comfort liner: Hey Dude Britt
We are big fans of the Hey Dude shoes and we are so excited that they offer an ankle bootie that is just as cute as they come. For $ 59.95, you get a faux fur-lined canvas bootie with a removable memory foam footbed and super light outsole (the entire boot weighs just 5.6 ounces). The Hey Dude shoes (including the Britts) offer a loose fit, ideal for feet with bunions and hammer toes. Find the Hey Dude Britt in a variety of colors and patterns in entire sizes 5-11 for $ 54.95 with $ 4.00 no-box shipping (or free shipping with purchases of $ 100 or more) and free returns from Zappos.
Finalist: Bzees Golden Bootie for $ 59 (available in large and has many 5 star reviews).
Best boot without leather: Bussola Chia
These cute and comfy ankle boots from Bussola are made from a slightly stretchy microfiber, making them tolerant of bunions and hammer toes – they’re water repellent too! The insole is lightly padded and the non-slip outsole is flexible. These slippers fit a bit small so order up to half, you may want to order one size up. Find the Bussola Chia in sizes 6-11 for $ 94.95 at Shoemall and Amazon.
Best wedge ankle boots: Sorel Evie Lace. I was about to include the hugely popular Sorel Joan of Arctic II Wedge collection in this post on the most comfortable ankle boots, but couldn’t get past three inch heels. So I saw that! The Evie features a 2 1/4 “wedge heel with a 3/4” platform, that is, a rise of only 1.5 inches. The upper is waterproof suede and the outsole is molded rubber. Available in sizes 5-12 (even a 10.5) for $ 140 at Sorel.com, Zappos, an Amazon. Discover the zipped version of the Sorel Evie here.
Best stylish ankle boot in several widths (even narrow!): Propet Reese
We are encouraged to see Propet branch out to design more stylish shoes. The western-inspired Reese boot features a rounded toe, removable footbed and shock-absorbing outsole. The Propet Reese is available in sizes 6 through 11, narrow to extra wide for $ 95 at Zappos, Amazon, and Shoemall.
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