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Over 50? Comfortable Shoes That Look Super Cute!

June 13, 2024

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I agree with the old saying, “The shoes make the outfit.” But for those of you who have been following TMG for a while, you know I have several autoimmune chronic pain conditions. One of them is inflammatory arthritis which also affects my feet. Now, I was never a stiletto girl. I wore heels when necessary or when I wanted to dress up, but I never wore any shoe styles over 3 inches. And now, that sounds like Mt. Everest. And frankly, even flat sandals or sneakers with no support or cushioning left me feeling like I could barely walk the next day. So I’ve been on a quest for the last 3-4 years to find comfortable shoes for older women that don’t hurt, but still look super cute. Because we ladies over 50+ do not deserve to relegate our sense of style and expression, just because our feet hurt! Put down those heels!



I have tried so many brands. So many styles, Sooooooo many. So I am going to start by sharing the shoe styles that work for me and my painful feet. But I also have a list of shoe brands that consistently develop shoes that are meant for comfort but don’t sacrifice style. None of those orthopedic shoes of the past my friends. I would wear these even if I didn’t have pain issues! And lastly, I have found the best shoe inserts that really help with comfort, and make a particular shoe you thought was unwearable, your favorite!

Note: I only recommend products I would use myself. If you purchase items through the links on my site, I might earn a small commission from the retailer. This is at no cost to you and does not increase your price for the item. Money earned from these commissions helps keep The Middle Girls running! Thank you for your support!


Shoe Styles for Painful Feet

Boots- Stylish Shoes for Older Women

So, I’ve always been a boot girl. I love the way they look, full stop. But I have noticed that as I started developing my chronic pain conditions, my boots were the one shoe I did not have to change. I think they give just the right combination of support for the ankle and also are not too tight to cause swelling and inflammation. Now don’t get me wrong. I had to add memory foam inserts to all my shoes as my arthritis and plantar fasciitis progressed to make sure they were comfortable shoes for my feet. But my boots are still my favorite shoe for both comfort and cute factor. And I think they are some of the best shoes for back pain and foot pain because of their low heel and support. I wear both knee-high and ankle boots depending on the season and outfit. Boots are stylish shoes for older women, period. And even though I don’t wear boots with high heels, I feel like they still add an elevated look to any outfit. Heels not required.



Flats for the Win!

Ok, this may seem like a no-brainer. But I’m one of those women that no matter what flat I choose, I get blisters. Either I have to wear socks so high that it ruins the look I’m going for, or I have to suffer. One hot summer I wore a pair to a restaurant in Sacramento, meeting our daughter’s boyfriend. “It’s just into the restaurant and out” I said. Unfortunately, being a midtown spot, we had to park several blocks away. By the time we got to our table, my heels were literally bleeding all over my shoes. I walked back to the car in bare feet.

But flats work as a shoe style for so many women, so I was determined to find a way.

  • First of all, take your low-cut socks with you when you shop. Every pair of shoes is a different height. You don’t want to buy a pair that are cut in a way where your sock can’t protect your ankle.
  • Buy ankle socks in the same color as your shoe, that way if they peek out above, no big deal.
  • Use back of heel protectors to prevent rubbing. Trust me, band-aids, even waterproof ones, will never stay put for long.
  • Most flats have no arch support and little cushioning. Use inserts.


Photo by Toms


White Platform Sneakers :  Not Just for 20 Somethings

Ok, sneakers seem like another no-brainer. The thing is, I don’t always want to look like I just came from the gym. Luckily, one of the hottest trends is wearing platform white sneakers with… well, almost everything. I have three pair. Another choice for stylish shoes for older women that are comfie too! Great shoes for back pain.


Photo by Chicos


Comfortable Wedge Sandals

Wedges can give you that heeled look without the heel pain, making them super comfortable shoes for dressing up a bit. They spread your weight over the entire shoe, rather than concentrating it in a spike heel. They also tend to be platform sandals. This means it may look like a 3-inch heel, but really it’s only 2 inches because both the toe and the heel are raised.



Block Heels for Older Women

On the rare occasion when I feel I really need to wear more formal heels, I go with block heels with a supportive strap. And I never go over 2 1/2 inches. The block heel means you don’t feel like you are going to fall off your own feet. And the more you can adjust the straps for a snug and supportive fit with these shoe styles, the less your feet have to compensate for being unstable. Which basically, means less pain.


Photo by DSW.


Mary Jane Style Shoes

Pumps for me were always like flats. Blisters on my heel. But Maryjane pumps have a strap that secures the shoe across the top of your foot, making for a better fit. Again, inserts and back of heels protectors. Bonus: They are trending in the fashion world.


Photo by DSW.


Shoe Brands for Women Over 50+

First of all, I didn’t just pick these brands off the internet and throw them into this post. I wear these super comfortable shoes. These are my fav pairs, right from my closet! ⬇



Ok, let’s break it down.

Clarks Shoes for Women

Boots, sandals, wedges. These were my first brand find when I knew I needed to find better quality shoes for my aging feet. They have non-slip soles, quality upper materials that don’t rub, and comfort footbeds. They have been on the cutting edge of comfort technology for 200 years. Yep, you heard that right. Did I mention cute? I love their wedges! This is the pair I own… Both in Coral and Sand! These are some of the best stylish shoes for older women, because they are designed for comfort.


Clarks Womens Annadel Eirwyn



My ankle boots are from Born. Supportive yet comfortable footbeds and quality materials that last. In fact, they look even better as they age!

They don’t sell my boot anymore, but I love this one! In fact, this will be my next!


BORN Kati Boot



Tom’s Womens Shoes

Super comfortable shoes; heels and flats. I’ve never tried their iconic Alpargata espadrille, but they are iconic for a reason! When you buy TOMS, you help fund access to mental health resources for the millions of people who need them. I’m in!

I love these block heels…


Milan Closed Toe Heel


And these flats!


Briella Flat



Vans Womens Shoes

This is my standard white platform sneaker.


Womens Plimsolls



Skecher’s Womens Shoes

Ok, Skechers Slip Ons are my favorite sneaker ever. Seriously, the most cushy and comfy shoes I own, you don’t have to bend over to put them on, and they are so “on trend” cute. I literally wear them everywhere. So far I’ve had mine for about a year and I’ve seen no significant signs of wear. And again, I wear them all the time. But even if they did wear out once a year, I would happily rebuy them. Best. Shoe. Ever. These are the exact ones I own… These are the best shoes for back pain I own because they are so comfortable I don’t find myself “guarding” to walk in them. That tensing of the muscles is a key player in my back pain.


Skechers Slip Ons Summits Dazzling Haze



Crocs Womens Shoes

Ok, I know what you’re thinking here. Crocs are not cute, IMO. But I do wear the Crocs brand flip-flops. They are the ONLY flip-flops I can wear. They have a cushy little spring of a footbed. And to be honest, my daughter visited recently and dared me to try her Crocs. Ok, they are so comfy. I see now why so many nurses and doctors wear them. Still not sure they are for me, but comfort-wise? 👍🏻 The flip flops I own are called Capri, and though they don’t make them anymore, there are TONS with the same springy footbed you can pick from!


Crocs Women’s Flip Flops



Gentle Souls by Kenneth Cole

So flat open sandals are one of the types of shoes that are hard to “cush out”. You cant use a full insert both because it would show, and in some shoe styles, it would not clear where the toe straps attach to the footbed. So these need to be good right out of the gate. My Gentle Soul flat leather sandals are comfy, age well, and are a great classic look for summer. Their shoes are exactly what they claim… Gentle on your foot. They don’t make my sandals anymore, but these are pretty close…


Womens Helen Flat Sandal



Best Shoe Inserts for Pain

So here is the deal…with my chronic pain, even the most padded footbed is sometimes not enough to make for comfortable shoes. Here are the shoe inserts and back-of-heel protectors I use. They allow me to wear the shoes I want, without walking with a cane the next day. 🤪


Happy Step Inserts

These memory foam inserts are perfect for closed shoes like sneakers. They do take up a bit of room as they have support and cushion, so don’t try them in shoes that are tight. I’ve compared them to the leading brands, and I think these are better.


Happy Step Inserts



Memory Foam Inserts for Tighter Shoes


Memory Foam Inserts



Summer Soles Inserts

Adhesive inserts for summer slides- My feet sweat in the summer, and that can make slides and certain sandals hard to wear. Who wants to be sliding all around in your shoe? Sweat can cause your shoes footbed to wrinkle and peel. These inserts are adhesive for open shoes and are so soft, kind of suede-like.



Back of Heel Protectors- Larger Shoes

Back-of-heel protectors – These are the best inserts for heel pain. I use these bigger ones for sneakers and boots, and these shorter ones for flats. They. Change. Everything. No more back-of-heel blisters and I can finally wear flats!!!



Back of Heel Protectors- Flats and Smaller Shoes



I hope sharing what comfortable shoes I actually wear (and love!) will help you realize that just because we are aging, it doesn’t mean we can’t have cute shoes! In fact, maybe we deserve them a little bit more?

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