The Best {Stylish} Comfort Shoes for Women

summer comfort shoes for women

By popular demand, this post is all about trying to find the best (read: stylish AND functional) comfort shoes for women. I will be focusing on summer shoes and sandals for this post. I can write another one in the fall.

I know I’ve posted about my comfortable shoe finds here and there, but several people have asked that I write a post dedicated to sharing the best comfort shoes for women that I’ve found. Sorry, men! You’re on your own.

I’ve definitely done plenty of “research” and, quite frankly, invested a lot of money in shoes this year! So someone might as well benefit.

My story: two years ago I developed plantar fasciitis. I assume it was due to running in minimalist shoes, but no one really knows. I’ve changed my shoes, been in physical therapy for a year, and finally stopped running altogether and NOTHING has fixed my finicky feet. In fact, they’ve only gotten worse.

As a result, I have had to resort to wearing “comfort shoes” all the time. This has been quite a game changer for this fashionista. I love shoes — cute shoes . . . flimsy flats, strappy sandals, sky-high heels . . . shoes that are not practical are what I love.


I’ve never had any trouble with my feet until this plantar fasciitis came out of the blue a couple years ago so this is all new territory for me. Also? if I’m not wearing cute shoes, I prefer to be barefoot. But with PF, you have to wear shoes all the ding-dang time. It’s been a big adjustment.

So here’s the breakdown. But please remember, everyone’s feet are different so what works for me might not work for you. I’ll try to give as many details as possible about fit and all that. For what it’s worth, my feet tend to be flat and a bit on the narrow side. Shopping links are provided for your convenience through my affiliate partners.

The Best Comfort Sandals for Women

Since it’s summertime, let’s start with sandals. I’ll include flip-flops in this category. Some people will advise never to wear flip-flops with plantar fasciitis; they say you need a back strap. I understand why; you definitely have to grip with your toes to walk in most flip flops, so it’s not ideal, but they make some really good ones and there are some times that I just want to wear flip flops (like every day in the summer, ha!)



I have just discovered Fit Flops and I already have two pair. A physical therapist recommended them to me when I told him I have a fashion blog. At first I wasn’t sure I liked the looks of them, but the styles are growing on me. They’re more on trend than most comfort sandals I’ve found.

For me personally, these have THE most comfortable footbed of any shoe I’ve tried. They are soft and squishy, and they have support without having an uncomfortable arch. My biggest (only) complaint with them is that they are made for people with thicker feet than mine so my feet slide around in them and it’s hard to keep them on. The top of the sandal does not even touch the top of my foot. So I wouldn’t wear them when I need to do a lot of walking, but they’re so comfortable that they’re now my go-to shoe for around the house. The days I wear these are the days my feet are the happiest. Yes, they’re even more comfortable than sneakers. Here I am, wearing the Pietra II.


Despite that, I bought a second pair. The second pair I got is the Skinny, and I chose it because it has an adjustable buckle that I can tighten (and I thought it would be fun to have gold sandals.)

FitFlop Skinny

Unfortunately the thong hurts my toes. It’s weird because the Pietra II is so incredibly soft everywhere. Nothing rubs. But the Skinny is rubbing in between my toes and it’s very annoying. I realized that it’s because I have the buckle adjusted so tight, it is pulling the thong to the side, and rubbing into my second toe. So unfortunately I think these are going back. Too bad, I had high hopes.

For those who do not have particularly skinny/flat feet, you will probably love Fit Flops. Just about everyone I know who has tried them loves them. Another downside, they are a bit spendy, but there  is a range, and the plastic styles are a little less. I cannot stress enough how very comfortable the footbed is.



Last summer I discovered Orthaheels at the recommendation of someone here on the blog, and since then I’ve heard a lot about them. They’re designed by a podiatrist and made with a lightweight biomechanical orthotic footbed that supports your feet and helps realign your lower legs. They do make flip flops, but once again, they are also too big and my foot slides around. I do, however, have two pairs of their sandals. They have a patented footbed technology that is also very comfortable, although I do find that the arch is a bit too pronounced for my personal comfort level. I have to get used to that and if I do a lot of walking, my arches hurt.

They make some cute styles, though. I haven’t checked this year to see if they’ve come out with anything new. I feel like the Fit Flops are a little bit more fashion forward, but the Orthaheels have more options at lower price points, and they do have many styles with back straps if that is important to you. I have the Julie in brown and the Mia in silver. I wear the Mia when I want a sandal and need to do a lot of walking. It stays on my foot without having a strap right across the top of my foot. I really like the styling on these.




I bought the Dansko Sophie Sandal earlier this spring after spending about an hour in The Walking Company trying on just about every sandal they carry. My biggest problem with comfort sandals is that there is too much space between the top of my foot and the shoe. I don’t understand why they’re all made so big. I can go into any shoe store any day of the week and find sandals or flip flops that fit, but when I try to find a comfort sandal, they all stand up a half inch off the top of my foot. SO irritating.

I chose the Dansko Sophie because it has two adjustable buckle straps that allow me to make them so they stay on my foot. There is no back strap, but they stay on so well that I don’t need it. My foot doesn’t move when it’s in these, although they’re buckled on the tightest setting so the straps kind of dangle over the sides, lol.

These are super-dee-duper comfortable. The arch is supportive without being uncomfortable, and they don’t rub anywhere or have any rough edges. I don’t find them as attractive as some of my other sandals, though, so I don’t find myself wearing them as often as I had hoped.


There were lots of others cute styles at The Walking Company. Their Abeo line is great, and I also like Umberto Raffini and Taos. It’s definitely worth looking around. And bonus! Right now, The Walking Company is running a HUGE Summer Sandal Sale with savings on Dansko, ABEO, ECCO & More! 

Other Suggestions

I can’t speak personally to most of these, but I asked on my Facebook Page, and these are some other styles/brands that people like:

  1. Teva (specifically the Mush flip flops): these are super casual, but they’re cute. I have never been able to wear Teva because they’re too loose. Story of my life . . .
  2. Birkenstocks are making a come back and they have some sassy styles, like the Gizeh. I’d be willing to give them a try for casual wear.
  3. Clarks: I know a lot of ladies who like these. I’ve found their styles to be a bit frumpy but at a quick glance on Zappo’s, they have some cute styles this year.
  4. Chaco: these are very athletic/outdoorsy, but I’ve heard great things.
  5. Born: a lot of cute styles here, not sure they have quite the support that I need, but they’re a good choice for people who want comfort but don’t have a specific issue like I do.
  6. Keen: Another athletic/outdoorsy style, but if you like that, these are great.

So I guess I don’t really have a sandal solution that I love at the moment. I guess that’s why I keep buying more! LOL.

The Best Comfort Ballet Flats & Pumps for Women

I still love my Cole Haan Milly Wedge Pumps. It’s my go-to for spring if I want a pump or flat. It has Nike Air technology and just enough of a heel to be flattering but not enough to be uncomfortable. In fact, it is just the right height for taking the pressure off my heel, where I have the most discomfort. Unfortunately the sandstone is no longer available. The silver is nice, but it’s not as summery. The red is pretty too.

Milly Cap-Toe Wedge Pump, Sandstone

I still like my Taos Untold ballet flats, although mine are black so not so great for springtime. They are most comfortable worn with the Abeo insert. A few colors are on sale at The Walking Company right now.

taos untold

My friend Jessie highly recommends the Teva Makena ballet flats. They’re cute but more casual than what I often need.

Teva Makena

Honestly, I don’t wear flats and pumps much at this time of year. I’m usually in sandals or flip flops. I have been wearing a pair of very old Stuart Weitzman wedge sandals when I want to dress up. They are actually super comfy, although quite high so I know not great for my back. Still, the wedge takes the pressure off my heel, which is where my pain is, so I’m going with it for now. There are times when a girl just needs to wear a high heel!


A lot of people recommend Toms. They are cute, and they may be comfortable, but they don’t look like they offer much support. I bought a pair of their wedges earlier this year, but they wouldn’t stay on my feet.

These platform wedges are kind of cute, though! They might be worth a try for something a little more fun.

Screen Shot 2014-06-13 at 6.43.03 AM


I’m not doing a section on sneakers because sneakers by nature are fairly comfortable. Some, however, have more support than others. It just depends on your needs and preferences. I bought the Ecco Biom Lite Flow Toggle at The Walking Company earlier this spring, and with an insert inside, they’re comfy, but my physical therapist didn’t feel they had enough support. He recommends me wear a supportive athletic sneaker with inserts, and now that I’m used to those, I can see how these have very little cushion and support where I need it. Le sigh…


They would work nicely for a lot of people, though. They’re very comfortable, and I think they’re rather cute too.

My friend Robin recommended the Reebok Skyscape, and they’re kind of cute for a fashion sneaker.

reebok skyscape

Gosh this turned into a book!

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This is not a sponsored post, however, some links are compensated affiliate links.


  1. says

    This is very helpful, Jo-Lynne. I developed PF after I started running as well. But I haven’t been very good about keeping my promise to my podiatrist to never go barefoot or wear flats. I hear rolling a small ice cold water bottle under your feet a couple of times a day helps. This is coming from a runner so I might give it a try. It’s so hard to find true comfortable and stylish shoes. I really do like the Fit Flops. I think I’ll need to check them out. Have a great weekend!

      • Joyce Padia says

        I too had PF and after a year or more of suffering and giving up all high impact activity, I stumbled on this: grasp a golf ball with your toes! I did this every night for a few weeks, and THE PAIN WENT AWAY! My doctor never heard of this, but I’m convinced it did the trick, oh and sticking my foot in the pool in December…maybe I just froze the nerve. Hope you find some relieve.

  2. says

    I didn’t realize there were so many stylish options out there! I think I commented before on how great Fit Flops are. Those ballet flats are really cute and I love the Tom’s wedges!


  3. Sue says

    Good Morning! I’m so glad you found the Fit Flops! I had a terrible few years with PF, even ending up with a stress fracture and as a result…but…I tried the Fit Flops after asking a cute lady in Costco what kind of shoes she was wearing (desperation!) because they looked like they would work for me and my shoe requirements :) They turned out to be Fit Flops, and they have been my comfiest shoes I own. I think they are better looking on the foot than in the box…and living in hot Texas, I can wear a lot of the year, but bought their black patent clogs last winter.. As encouragement to you, my PF is now completely gone, for no apparent reason, although it did improve vastly once I finally decided to choose the right shoes and rest. The PT, cortisone never really seemed to do much good, at least long term. I wear my flat sandals every now and then, but can tell after a day on my feet that I’d better be careful…so I go right back into Fit Flops. Good luck with your PF- my experience is that with a severe case it is not a quick fix, as you also know. But hopefully it will get better! Keep wearing those Fit Flops!

    • says

      Thanks for the encouragement, Sue. I am doing nothing right now – no PT, no stretching, no anything. I am uncomfortable but it’s not unbearable pain so I’m putting off any further treatment for a while and just trying to rest and wear sensible shoes for the most part. I bought a bike and cannot WAIT to ride that. I hope it will give me the enjoyment of cardio and being outdoors without the damage to my body that running causes. Maybe one day I can run again, for short distances. I am hopeful!

  4. says

    Woo hoo! Love my Birks and lived in these for years. Some people think they aren’t very chic but I get tons of compliments and they go with anything – shorts, boyfriend jeans, dresses, skirts, etc. I have friends who wear FitFlops too but I’m afraid my foot would move around too much with a wedge and a thong. May have to give these a try. Great post!

  5. says

    I have problem feet and just bought my first pair of Fit Flops after hearing multiple recommendations from friends. I really like when you show “comfort” shoes in your fashion posts, because they look great and remind women that you can still look stylish even with this type of shoe. It also helps that they’ve become way more stylish the past few years!

  6. says

    So sorry to hear about your struggles. You have found some great comfortable and stylish options though! And you can’t beat that combo! I recently bought a pair of Birkenstocks myself, and I love them! Thanks for hosting!

    xo, Amy Ann
    The Real Arnolds

  7. Beth says

    Ok, some of those orthaheels are cute, and cheaper than I expected them to be. Now I just need to get work to carry them so I can get my discount! The price isn’t bad when I take off my discount, I can’t convince myself to buy shoes anywhere else though. Plus I hate being at work and having to tell people no, we don’t carry what I’m wearing.

  8. says

    I live for a stylish comfortable shoe. Taking notes on these. Thanks for this post, Jo Lynne – you always have the best fashion advice.

  9. Elizabeth says

    Thank you so much!!! I’m suffering from PF also & had no clue where to get appropriate shoes… You’re a lifesaver!

  10. Evelyn Johnson says

    I have had PF for about 14 years (even had the surgery) and had to give up running….I still miss it to this day! I did start cycling/spin classes and love it! It is the closest thing to get my heart rate up as running did. I hated that I couldn’t wear some of the cute shoes although shoes have definitely come along way since 14 years ago. Another thing that has helped me was Happy Feet insoles…love them! I can wear most shoes now as long as I slip a pair of Happy Feet in my shoes. Another pair of shoes that I discovered last summer where Keens….very comfortable! You can wear them hiking, in the water, and just around town. I even throw mine into the washer and they still look great after a year.
    Thanks for the update on the different shoes. It’s always great to see different shoes.

    • says

      Ugh, I do fear that is my fate. I can’t believe how much I miss running. It is almost like losing a friend. I know that sounds bizarre, but it is so hard. Anyway, I got my bike, so I’m hoping that will become my new passion. :-) I do like Keens and I have a pair. My PT also recommended them. I’ll add them to this post.

  11. says

    Jo Lynne, this is my first time linking up but I follow and read your blog often. You have great Mom Style and as a Mom I love that. I agree about Comfy Shoes especially for Summer with all the heat and your feet sweating and all. You have some great wedges & sandals.

    Would love for you to stop by my blog and check out what I linked up. Thank you & Enjoy the weekend. Ada. =)

  12. says

    I am sorry about your condition, Jo-Lynne. Your post gives some hope to people with PF. I like the Orthaheels, and, mostly, the Reebok Skyscape. Great options you have here!

  13. Mindy says

    Thanks for this. I, too, have problem feet. I am struggling to find comfortable dress shoes and how to pair with business apparel. I have a pair of wedge, round toe pumps like your cole haan, but even those after a day or two start to hurt. Keep highlighting finds and suggestions of how to wear comfortable shoes in an office setting, please oh please.

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