Comfortable Boots for women

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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

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!

comfortable ankle boots : Munro Brittie

Munro Brittie

Most comfortable ankle boots with a heel (and come in narrow to wide widths): Munro Brittie.

This is one of our favorite styles by Munro, who specializes in hard-to-fit feet! The velvet laces add a festive touch to this vintage-style bootie. A removable footbed may allow for a personal orthotic. A happy Zappos customer says this about her new comfortable ankle boots by Munro:

LOVE these boots. WOW. I got the black leather. They are stable and comfortable, and they look great with jeans. I’m not used to 2″ heels for everyday but these are fine. Removable footbed and my Superfeet insoles fit.

Find the Munro Brittie in black and ruby red patent in sizes 5-12, super slim to extra wide widths for $149 from Zappos. For other brands that specialize in extended sizes and multiple widths, check out the Drew Kool and ankle boots by brands Aravon, Dr. Comfort, Apex and Walking Cradles.

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!

comfortable ankle boots - taryn rose babson

Taryn Rose Babson

Best comfortable office-appropriate ankle boot: Taryn Rose Babson

This sleek ankle bootie features a 1.5″ sculpted demi-wedge heel, contoured arch support and a cushioned ORTHOLITE footbed for all-day comfort. A water-resistant upper makes the Babson a good option for commuting in wet weather. Available in sizes 4-12, medium and wide widths for $84 from Amazon.

Bussola Cyra Coimbra

Bussola Coimbra / Cyra

Bussola Cage

Bussola Cage microfiber boots

Best non-leather ankle boot: Bussola Coimbra / Cyra

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 Coimbra (sometimes named Cyra) in sizes 6-11 for $94.95 from Shoemall, Amazon and eBay. Coldwater Creek carries a mid-calf version of this microfiber boot by Bussola.

Best wedge ankle boots - Sorel Evie

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.

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

  1. Donna says:

    I have had a fusion for Hallux rigidus. The Dansko Frankie is a pull on style. Can it be pulled on or am I best to look for a zipper that allows the non-flexing joint to put the shoe on and off? Any other alternative with a zipper out there?

  2. Noreen Holloway says:

    Hi, can you tell me about the purse/tote that is in the picture with the Dansko Joy?

  3. 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!

  4. Jo-Lynne Shane says:

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

  5. Lette says:

    The Archopedico N42 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. 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.

  7. KKH says:

    Having narrow heels and wide forefoot is difficult. Add some additional forefoot problems and it’s near impossible to find a solution! I bought the Romika boots and sadly, the forefoot is terrible. I had foot surgery last year to remove a bunion and fill a cyst. Was hoping that I could wear the Romika this year however, I now have top of foot pain and having any pressure there is not tolerable. I’m only 37 and I’m jealous of the grannys in the grocery store who can at least where a loafer or a cute flat. Kristen, I have to say, I think we need an extra arm of this site for the truly difficult cases. Why can’t a 3D printer just create customized shoes that I could wear in a professional setting? Obviously, your site has proved there is a vast market of people who are in pain.

  8. Janice says:

    I have tried so many shoes it’s almost heartbreaking. My main go to is Birkenstock but I would love to have something in a boot for my painful feet. Have had heel spurs, I have an issue with the ball of my feet therefore I cannot wear any heals and bad knees. I am falling apart!! If I spend any length of time on my feet I usually end off of them the next day due to the pain. Can you make any suggestions please?

  9. Marte says:

    Why are my Romika shoes falling apart?

  10. Tracey C says:

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

  11. 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.

  12. Beverly B. says:

    Hi. Please remember that some of us have wide feet! Please consider doing a parallel review, for example, about ankle boots that also come in wide widths. I looked up each boot in this post and NONE of them are available in wide widths.
    I like your site but I would like you to note the WIDTHS of the shoes you review. That would be greatly helpful. Thanks!

  13. 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!

  14. 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?

  15. 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.

  16. 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

  17. Turk says:

    Nice article!

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