Cute Supportive Flip Flops #RunnerProblems

So this is my new mission — to find cute supportive flip flops to placate my finicky feet. Even while I’m wearing the boot, I need something for my other foot with a bit of height to it so I’m not lopsided, and I know once I’m out of the boot, I will be required to wear only super supportive footwear.

My PT recommended Fit Flops so I looked them up and I just ordered a pair. They’re fairly cute, yes???


I chose the Pietra II, but they have quite a few styles. (This post is not sponsored, but as always, I’m using affiliate links when featuring products available for purchase.)

pietra II

Then these Sam Edelman ‘Annalee’ Thong Sandals showed up in the sidebar under the “People Also Purchased” section. These websites are smart because I ordered a pair of these too! I don’t plan to keep both. We’ll see how they fit and feel.

Sam Edelman 'Annalee' Thong Sandal

And there’s always the Orthaheel. I like my Orthaheel sandals, but their flip flops don’t fit my flat feet very well.


Do you have cute supportive flip flops that you recommend? Link me up!

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29 Responses

  1. You’ll love the fit flops … I think I have about 6 pair now (some dressy, some plain). I’ve walked Disney World and many other heavy walking trips in them.

  2. I had several pairs of the Fit Flops and LOVED them…but then my achilles tendons went all to hell and my PT told me that the unsteady surface of them and flip flops in general were probably much to blame for my problems. Sigh. Seems that the cushy awesomeness of them also put a ton of strain on my stupid weak ankles. But I so so so loved them and I am super sad that I am not allowed to wear them anymore…

  3. Fellow Plantar & Bone spur sufferer here! I have had great luck with these the past few years – currently they are my ‘house slippers or morning shoes’ but I do wear them out to beach and grocery too! CHACO Vibe Flip Flop

    Can be found on sale many places.

  4. You are killing me with these great shoes that are out of my price range! =). For me a wedge flip flop goes a long ways.

    1. Oh no, I’m sorry. I’ve been trying to do better about featuring more moderate price points as well. The Orthaheels aren’t as much, I don’t think. I’m kinda hoping the Fit Flops don’t fit b/c that’s a lot of $$ for shoes I don’t love. LOL.

  5. I just got my first pair of Fit Flops because I have had them recommended to me so many times by friends. I’ll be on my feet many hours a day once swim season starts, so I needed the support.They’re kind of boxy-looking, and I have big feet, but if I want the support I guess I need the wedge thing. I like the Orthaheels you had on in a post the other day. Much prettier than the Fit Flops!

  6. Last summer I was having a hard time with plantar issues. I wore only my asics and fit flops. It seemed to get worse. I went to an orthopedist who told me to just wear my asics. Still didn’t help. I decided to go barefoot for awhile only inside of course and it cleared up. I loved my fit flips, but think it had too much arch support for me. Hope they work for you. Love your blog!

      1. Yes, Jo-Lynne, it is very hard. Since most of these types of shoes are special order, one has to be patient. The Ortho-Heels are great in styling but have too high of an arch for me, I’m finding. Had them recommended by my podiatrist. I’ve been referred to your blog bc I understand you have problematic feet! 🙁 I FEEL YOUR PAIN, I do!! Thanks for sharing your findings. I SOOOO appreciate it!!

          1. No, but will check into it…was a bit hesitant as one reader said it was to high of an arch…should this be a concern?

  7. I NEVER ever thought I’d wear Birkenstocks, but last summer I tried a pair of their Gizah Berka-Flor sandals which is more like a t-strap flip flop and fell in love with them immediately. I have plantar fasciatis flare ups too and these have not aggravated me at all, even after wearing them on long days in NYC last September. No, they’re not dainty but they have a strangely hip vibe to them–and they are comfortable (I did have to get used to the footbed at first since it’s a hard cork with ridges but after a few wearings they were fine). I have them in black.

    But I am NOT a hippie. 🙂

  8. Just a heads up the Pietra link is broken. My favorite flip flops are a pair of skechers I’ve had for years so don’t know that I’m much help!

  9. I struggled with plantar fasciitis for a good year…very similar story to yours. Ended up not running for 6 months, and lived in big clompy stability running shoes-no bare feet allowed. Had PT (graston therapy)to break up the huge amounts of scar tissue in my foot. Someone gave me a pair of fit flops to try. I wasn’t thrilled with how they looked, but wow! They were very comfortable, and I ended up wearing them around the house as well. My foot is fully healed now, and I was able to do a half marathon on it with no trouble. I think the fix was finding the right combination of things, including PT and tons of calf stretching, but finding footwear that helped definitely played into it. Size 10 fit flops aren’t the most flattering look in the world, but my feet are sure happy in them so who cares !? Everyone’s feet are different, but I’d recommend giving them a good try!

    1. So there’s hope? LOL!! I have done all that tho, and it didn’t work. I do think my daily footwear has played into this issue. But also, my guess is I didn’t take off from running long enough. When I was feeling better, I wish I’d had better guidance as far as starting to run again. How gradually did you go, getting back into it? When did you start back and how did you know it was okay to start again? Thanks for the encouragement.

  10. I have several pairs of Fit Flops and love them! I usually get a new pair every summer. They are really comfortable but cute too!


  11. I have bad knees and love fit flops! I have five pair in different colors…..here are my favorite ones! https://m.zappos.com/fitflop-flare-leather-black-leather. Already have pebble, gray, black, just purchased navy this year:). I tried a nude wedge you recommended from nordstroms but they werent nearly as comfortable as my fit flop so I sent them back. I get compliments on the sparkly ones all the time!!!

    1. Which nude wedge? The Sam Edelman? No, they’re not really comfort shoes. I mean, I think they are comfy if you don’t have foot issues, lol. But I think fit flops would be much different. I can’t wait to try them!

      1. Yes that was the one! You wont believe how comfortable they are!!!! Granted not as dressy as the wedge. Cant wait to hear how you like them!

  12. Do Orthaheels run really big? I bought a pair from a resale site that said they were 7s, but they feel really big to me. I like the support but I guess I need to size down. The Fitflops are cute, too.

  13. I’ve been “managing” Plantar Fascitiis for 3+ years. I didn’t get it under control until I completely gave up flip flops – all kinds. I now only wear sandals that include a strap that goes up around my ankle and my foot has thanked me for it. The T-Strap Birkenstocks another reader mentioned are awesome and are cute. I still wear a boot to bed every night, but I have it under control and can work out.

    1. Hi Helen, just click on the links to the ones you like and it will take you to the website where you can purchase them. I wrote this post a while ago so some may have sold out.

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