Comfy Shoes For Feet Over 50

I shop all over the place and like you, I’m more likely to have better success at some retailers than others. Some women my age find treasures at Forever 21 but I’m not one of them. Now if there were a Forever 51… I might have better luck.

I hate to sacrifice style for comfort in my shoes so today I’m sharing a few brands who combine them well.


They have been in business since 1825! I bought my first pair of Clarks last spring and they won’t be my last. These have a lightweight cushioned wedge that gives me a bit of height but is only equivalent to 1/2″ heel. They close around the ankle with a Velcro closure in back so I can adjust how snug I want them.

Clarks has innovative underfoot cushioning and is constantly working to make shoes which keep feet healthy and feeling comfy.


They make super comfy boots, shoes, and sandals. I have a pair of their classic Sheepskin Shearling Lined Short Boot and love them. I wore these sandals in silver all summer and they were as comfortable as slippers.

Jennifer Connolly of A Well Styled Life wearing UGGS from Macy'sThey run wide which works for me because I have a wide foot. These driving moccasins look great for spring and come in seven colors.

Gentle Souls

I started buying this brand many years ago. Their website says “they care for your feet while combining fashion and comfort”. Most have rubberized outsoles, cork midsoles, flaxseed footbeds, and Poron® performance urethane padding. All that is to say, they are very comfortable. This was my first pair of Gentle Souls which I wore to death! I love the arch support, soft leather and their ergonomic fit which redistributes pressure for ultimate comfort. I have the earlier version of this flat which is the perfect all day shoe. And how pretty are these for summer?


I have several pairs of their booties and wear them often. Munro shoes and boots are available in 19 sizes and 5 widths to guarantee you can get the correct fit for your foot. I should have bought two pairs of these because they’re no longer available and I love them!Jennifer Connolly of A Well Styled Life wearing Bee Hoodie from Artful Home

Their heel heights measure the elevation of the heel above the ball of the foot, not from the floor which indicates the podiatric impact of a shoe on the foot. Amazon has a large selection of Munro here, as does Zappos here,  and of course, Nordstrom…where most of mine are from.

Eileen Fisher

I need to pick and choose which garments flatter me at Eileen Fisher because many of their silhouettes are too voluminous on me. But their shoes are a different story. They fit my foot, lifestyle and are super comfy. I bought my first pair several years ago during a marathon shopping day. Jennifer Connolly of A Well Styled Life wearing Eileen Fisher BootiesMy sore tootsies couldn’t walk one more step and blisters were forming. I passed the Eileen Fisher table shoe table and left wearing a pair. They’re soft leather, roomy and have lots of cushioning. These aren’t budget shoes but they aren’t astronomically priced either and you can usually find them discounted throughout the year.

Jennifer Connolly of A Well Styled Life wearing Eileen Fisher shoes

I have since added several pair of booties and sandals which I can rely on to always be comfortable.


This is a Danish shoe company who has been making shoes for over 50 years. They make shoes for work and play. So far I’ve only tried their sneakers. Wearing sneakers outside of the gym is a very new concept for me. I always felt they were cumbersome and unattractive but this pair sold me on the concept. They have a removable insole which gives you room to add your orthotics.

I now have these sneakers in black, white and recently added this rose dust color for spring. I also spotted a gorgeous blue pair and anticipate owning more of this shoe in my future. Fashion sneakers are all the rage this spring and they fit my casual lifestyle.

When I was working retail and standing all day, I invested in Beautifeel, Thierry Rabotin, Taryn Rose, Arche which I still wear to this day. Shoes can often make or break my day, so comfort is key but I still want them to be stylish.

Do you have brands you recommend?

Thanks for reading and have a great day.





This post may contain affiliate links which won’t change your price but will share some commission.
This post may contain affiliate links which won’t change your price but will share some commission.


  1. Cynthia
    May 8, 2019 / 4:13 pm


  2. Libby
    March 7, 2019 / 7:37 am

    I have Morton’s neuroma in the ball of my foot so need lots of cushion. I use Hoka One Ones for walking (I walk 10K per day) because they are so well padded. I took them to Europe for sightseeing. The other shoe that works for me is Fly London which have a tick rubber sole that I find to be a “shock” absorber. another more feminine brand is L’Amour des Pieds.
    Thank you for all your recommendations and those of your readers. Many thanks to all.

    • March 7, 2019 / 11:19 am

      I have one pair of L’Amour des Pieds and love them! I will look for Fly

  3. Susan
    March 7, 2019 / 6:30 am

    I am also thankful for your article, Jennifer. For years I struggle with hip pain and only recently discovered my uneven hips were due to my shoe choices! Who knew? I have a couple of comfy Clarks sandals and one pair of boots. My issue is wearing a size 5. Difficult to find and rarely is a pair left that’s on sale. Why are so many “ comfort” shoes so incredibly ugly? And bulky?

    • March 7, 2019 / 11:21 am

      Size 5 is a tough size to find. I don’t know why so many are ugly but they needn’t be

  4. Sarah K. Carter
    March 6, 2019 / 8:13 pm

    80% of my shoes are from Born, and some of them are 10 years old and going strong. Boots, booties, oxfords, slip-ons, loafers, driving moccasins, sandals…you name it – it’s available in Born. Stylish, comfortable, well made, and durable. (And no, ….I have no ties to Born financially!)

  5. Eileen
    March 6, 2019 / 7:29 pm

    Thanks Jennifer,
    I have been on the hunt for comfortable shoes. Following two hip surgeries and one laminectomy (with more due), I have been unable to wear my former stylish brands. The only comfortable brands I have found so far are Vionic and (gasp) Stuart Weitzman. I was so happy to have found them, because walking shoes just don’t work at a wedding reception.
    You have given me more brands to try. I may start with those cute Eileen Fisher ones.
    Thanks again for thinking of us ladies who stil want to look stylish even with our imperfections.

    • March 7, 2019 / 11:55 am

      I’m glad you’re here Eileen!

  6. Pearl
    March 6, 2019 / 6:53 pm

    Also, a lifesaver, and I’m not exaggerating, look up calf stretching at angryorthopod.com .
    The post is Calf stretching:it’s the AO way or the highway.
    If I post the link it doesn’t seem to work. It’s miraculous, just do it.

    • March 7, 2019 / 11:54 am

      Stretching is so important. Physical therapists have my husband several times a day for foot pain

  7. Pearl
    March 6, 2019 / 6:46 pm

    My daughter dresses more for work and loves Earth shoes. I have very special feet and a very casual lifestyle and it’s Naot or New Balance. We both like Jambu and J-41.
    Thanks for this, always need shoe ideas.

  8. Patti
    March 6, 2019 / 6:25 pm

    Born are great boots and super comfortable. I saw those mentioned already in a few posts. My go-to faves for heels are Vince Camuto. Very comfortable for heels, which I still love and wear, and I always get compliments on my Vince’s. I bought my first pair of Vionics, heels recently, after a recommendation from a young teacher friend of mine. Comfortable and stylish. Will definitely purchase another from this brand. For sneakers (not the workout variety), I love Sperry.

  9. Joan
    March 6, 2019 / 4:05 pm

    I wear SAS shoes also. They have really turned their styling around. Their shoes are comfortable and last a long time. Great for men’s shoes also and all made in America!

  10. Kay
    March 6, 2019 / 2:13 pm

    I have been wearing Gentle Souls for years. I wore out a pair and then bought one just like it! I like Eileen Fisher shoe styles, but they just don’t fit me right. I have gotten more picky about fit in my old age. LOL.

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