Comfortable Boots for women

Published on November 17th, 2021 | by Kirsten Borrink


6 Cute, Comfortable Ankle Boots Bring Blissful Relief to Problem Feet

Ankle boots have established themselves as a wardrobe staple deserving of top-shelf status right next to tall boots. In fact, I find I gravitate toward ankle boots as a more versatile and comfortable option to tall boots (I recommend Jo-Lynne Shane’s style primer on how to wear ankle boots if you’re still wondering). Have you found a pair of stylish, comfortable ankle boots yet? The ones that cradle your foot, fit like a glove and look great with your cool-weather wardrobe? With the thousands of ankle boots online and in store, it’s mind-boggling trying to decide which one will work for you and your particular foot issues. Let us help you narrow the search with our round-up of 6 comfortable ankle boots for everything from plantar fasciitis to hallux rigidus. And if you still can’t find what you want, check out our lively discussion about comfortable ankle boots on our Facebook page!

Comfortable Ankle Boots - Naot Helm

Naot Helm in ink leather/midnight suede

Naot Helm

Most comfortable ankle boots for plantar fasciitis: Naot Helm. Take it from Zappos customer, Sharon:

I’ve been struggling with painful plantar fasciitis for over 2 months; shots from a podiatrist; have given away several pairs of shoes and so much time spent looking for and returning any types of shoes I could wear (yes – and different supposedly orthopedic insoles). These are the only ones that I have been able to wear without pain and actually walking normally instead of limping.

We love the Naot Helm’s ability to perfectly combine a fashion-forward aesthetic with orthopedic comfort. Find the Naot Helm in six beautiful colors, euro sizes 35-43 (4-12) for $199.95 from Zappos. See our educator review of the darling Naot Kahika bootie for another comfortable option with rounded toe box and a more “relaxed” look.

Comfortable Ankle Boots - Dansko Barbara

Dansko Barbara

Dansko Bettie

Dansko Bettie

Best ankle boot for hallux limitus or rigidus: Dansko Barbara.

If you have hallux rigidus (painful big toe due to injury or arthritis), you’ve most likely been told to wear a shoe with a firm sole to keep the big toe from flexing too much. But sometimes rigid-sole shoes can feel hard and unforgiving to aching feet and toes. Thankfully, the Dansko Barbara not only features a thick (yet lightweight) outer sole with rocker motion, the footbed is generously cushioned with memory foam. The toe box is roomy to accommodate sensitive toes. Find the Dansko Barbara in euro sizes 36-42 (5.5-11.5) for $170 from, and  Zappos.

The adorable Dansko Bettie is similar to the Barbara, but with a fold-down shearling collar! Find it at and Zappos.

Don’t forget Fitflop ankle boots if you have hallux limitus or rigidus. Most feature thick, cushioned soles with roomy toe boxes. The styles keep getting cuter and cuter!

Hey Dude Britt

Comfortable ankle boots Hey Dude Britt

Hey Dude Britt

Best affordable comfort bootie: Hey Dude Britt

We’re huge fans of Hey Dude shoes, and are thrilled that they offer an ankle-high bootie that’s just as cute as they come. For $59.95, you get a faux-fur lined canvas bootie with removable memory foam footbed and super lightweight outsole (the whole boot weights in at a mere 5.6 ounces). Hey Dude shoes (including the Britt) offer a roomy fit, which is great for feet with bunions and hammertoes. Find the Hey Dude Britt in a variety of colors and patterns in whole sizes 5-11 for $54.95 with $4.00 boxless shipping (or free shipping with purchases of $100 or more) and free returns from Zappos.

Runner-up: Bzees Golden ankle bootie for $59 (comes in wides and has many 5-star reviews).

Bussola Cyra Coimbra

Bussola Chia

Best non-leather ankle boot: Bussola Chia

These cute and comfortable ankle boots by Bussola are made from a slightly stretchy microfiber which makes them forgiving of bunions and hammertoes–they’re also water-repellent! The insole is lightly cushioned and the non-slip outsole is flexible. These booties run a little small, so order up a half you may want to order up a size. Find the Bussola Chia in sizes 6-11 for $94.95 from Shoemall and Amazon.

Comfortable Ankle Boots - Sorel Evie Lace

Sorel Evie Lace Bootie

Sorel Evie Lace

Best wedge ankle boots: Sorel Evie Lace. I was just about to include the ever-popular Sorel Joan of Arctic II Wedge collection to this article on most comfortable ankle boots, but couldn’t get past the three inch heels. Then I saw these! The Evie features a 2 1/4″ wedge heel with a 3/4″ platform–that’s a rise of only 1.5 inches. The upper is made of waterproof suede and the outsole is molded rubber. Available in sizes 5-12 (even a 10.5) for $140 from, Zappos, an Amazon. Check out the zip-up version of the Sorel Evie here.

Best stylish ankle boot in multiple widths (even narrow!): Propet Reese

We’re encouraged to see Propet branching out to design more stylish footwear. The western-inspired Reese ankle boot features a rounded toe, removable footbed and shock-absorbing outsole. The Propet Reese is available in sizes 6-11, narrow to extra wide for $95 from Zappos, Amazon and Shoemall.

About the Author

24 Responses to 6 Cute, Comfortable Ankle Boots Bring Blissful Relief to Problem Feet

  1. Kirsten Borrink says:

    Great to know, thanks!

  2. Roberta Stasyk says:

    I LOVE the Josef Seibel Faye 05 boot so much I bought two pairs last fall. This fall I stayed with Josef Seibel and purchased the Sienna 59 Chelsea boot – it’s just as comfortable as the Faye boot! Thanks so much to Barking Dog Shoes for all the great recommendations!

  3. Jo-Lynne Shane says:

    Thanks for the shout-out! It’s good to see your blog still going strong. 🙂

  4. Kirsten Borrink says:

    You betcha! You have a good thing going!!

  5. Lette says:

    The Arcopedico L19 is butter-soft leather, so it doesn’t rub sensitive parts. Supportive, tiny little heel, and doesn’t skid out in wet weather. I’ve had them for a couple years and adore them. I’m sure I must have heard about them here at some point!

  6. Kirsten Borrink says:

    Thanks for the tip, Lette. Arcopedico is a wonderful brand.

  7. cedar says:

    The Romika Citytex 121is my go-to boot in Winter, during less than perfect weather. Waterproof, secure footing, looks cool with leggings or jeans. It has a more slender look, as opposed to chunky. It does run slightly narrow, but I have a medium width foot that leans wide (but I don’t need wide width) and it’s fine for me. I wear my usual size 8, but I couldn’t wear a thick sock with it, just thin to medium.

    I’ve been in the hunt the last month for a new bootie, and have tried several. I have fallen head over heels for Reiker Daphne 44252. I always have great luck with Reiker. I love the wool insole, and the shearling lining. I don’t like cold feet! This bootie is so lightweight, comfortable, quality craftsmanship. Stable sole, and no slipping. I bought the Black/Smoke color and love it. I wish it came in Navy, too. Runs TTS.
    I liked the Reiker Chandra, too, but found the Daphne 44252 to be more versatile.

  8. Kirsten Borrink says:

    Thanks, Cedar. We can always count on you for excellent tips and recommendations. xxoo

  9. Tracey C says:

    Thank you for this! I am a 10.5 wide, and do feel forgotten. Many great options here!

  10. Jennifer says:

    Has anyone tried the new Birkenstock chelsea boot? I have hallux limitus and need a shoe/boot with a wide toe box and stiff front, but something cute to wear to work. Kristen, thank you so much for publishing solutions and giving a voice to all of us with problem feet.

  11. Claire Thompson says:

    I have arthritic “bumps” on the top of both feet. Boots press down on them and cause lots of pain. Any ideas what boots or booties would work?
    Right now I am wearing fit flops , the slip on mesh now. Won’t work in the winter!

  12. Kirsten Borrink says:

    Beverly, I meant to include this one by Rockport Cobb Hill! A wonderful bootie in wide widths that many customers love for it’s support and cushioning:

  13. Kirsten Borrink says:

    We don’t forget our wide width friends, we just didn’t include one in this specific post. Here’s another one that comes in wides:

  14. Kirsten Borrink says:

    Claire–this one by Bussola is made of a soft, microtec fabric that glides over the foot–I think it would feel good on your feet.

  15. annie says:

    I wear a size 8 – 8.5 W shoe. I have been searching for well-made, affordable, fashionable shoes. I was so disappointed to see only one wide boot listed in this post. Does the shoe market believe fashion is only for women with narrow and medium width feet?

  16. Kate says:

    Hi. I have thick calves and ankles. Are there any ankle boots that have a wider opening so they don’t rub against my skin? Thank you in advance for your help.

  17. Kirsten Borrink says:

    Take a look at the top-selling wide width ankle boots at Zappos. I believe the shoe market is getting better and better at catering to wide-width feet, narrow, not so much. Earth brand has some super stylish ankle boots in wide.

  18. Suzanne Jablonski says:

    Hi I have Anterior Ankle Impingement. Which is arthritis in the front of my ankle. I need a ankle boot that will offer support but not press against it. Any suggestions

  19. Turk says:

    Nice article!

  20. Victoria Nelson says:


    Broke my ankle 2 years ago and need support for that as well as flat feet and deep padding for forefoot. I’ve tried many pairs of shoes & boots from Zappos but the only thing I’ve found to fit me ( size 10 1/2 Wolky’s Rosa) shoes. They felt great for about 20 minutes. Then my ankles started to swell and I realized there was no padding in the metatarsal region. Help! I need a winter boot or shoes. Any suggestions.

  21. AW says:

    I just ordered blundstones (the stout water resistant from Nordstrom) learning the half sizes are for width not length (so an 8.5 is an 8w). And they have a removable insole so they fit my custom orthotics! Haven’t tried them in the elements yet but so far I’m over the moon with them.

  22. Kirsten Borrink says:

    Wonderful! I’ve heard such great things about Blunnies from people with problem feet!

  23. Anna says:

    I have wide feet, morton’s neuromas in both feet. I have found that the Hey Dudes are absolutely wonderful!! So comfy and plenty of width for my wide toes!! Plus, most of them are also machine washable!!! Can’t beat the price either!

  24. Colleen says:

    Hi everyone,
    I am at the point of desperation with shoes.

    Does anyone know of a non-sneaker that works for high arches, hammertoes, arthritis – top entire left foot, and Morton’s neuroma on the right?

    I’ve been told I need a non-bendable bottom sole.

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