10 Fashionable, Comfortable Shoes

With so much emphasis on platform shoes in recent years, those who avoid heels are left wondering what to do. What can you wear if you’re not a fan of high heels, or if your spirit is willing but your feet are not?

Fortunately, you have lots of options – that DON’T look like orthopedic shoes. All it takes is a little digging online.

Here are ten comfortable, fashionable shoe brands that you can turn to for your work, casual, commuter, or social shoe needs:


Aerosoles are my walking shoe of choice. Not only do they come in a variety of styles and colors, they do not exacerbate my old dance knee injury when walking long distances. A real plus when doing the “tourist thing” in places like New York, New Orleans, San Francisco, and the like.



Anne Klein ShoesAnne Klein Shoes

Anne Klein has long been known for their classic clothes, but they’re also rapidly becoming a favorite of comfortable shoe aficionados. Their “iflex” series features softer, thinner leather with extra padding, which means they’re more flexible than traditional dress shoes, and therefore, more comfortable. They’re also reasonably priced (under $100), which is why devotees load up on their favorite styles.


Clarks ShoesClarks Shoes

Clarks was the first shoe company to produce a casual shoe back in 1949. It was an immediate hit, and Clarks had been the “go to” place for comfortable shoes ever since. Try their flats, boots, or walking shoes for a truly amazing experience.



Cole HaanCole Haan 

Boots, flats, heels, sandals – Cole Haan has them all. No, they aren’t cheap, but yes, they ARE comfortable. Invest in simple, basic styles that you can wear for years.





Me Too ShoesMe Too

Me Too also combines comfort with fashion for a nice selection of both classic and trendy styles. They have a wide selection of flats and booties.



Munro ShoesMunro Shoes 

Munro Shoes run wider than most brands, which is why they’ve been popular with walking enthusiasts for years. With widths from SS (Super Slim) to WW (Wide Wide), you’re sure to find a favorite style that fits your foot.



NaturalizerNaturalizer Shoes

I remember when Naturalizers were the first choice for the over-60 crowd. They weren’t pretty, but they were comfortable. These days, comfort and style go hand-in-hand at Naturalizer. Try them whatever your age or lifestyle.



SofftSöfft Shoes

Söfft Shoes have been putting comfort first since the 1920’s and have generations of devoted fans to prove it. Flats, booties, heels, wedges – you’ll be delighted by the selection.




Stuart WeitzmanStuart Weitzman

Stuart Weitzman is one of the few big designer names who’s actually known for their comfortable shoes. Try their flats, wedges, kitten heels, or low-heeled boots and you’ll know why they’re so popular.





Taryn Rose ShoesTaryn Rose

Created by an orthopedic surgeon, Taryn Rose has a cult following from lovers of comfortable, stylish shoes. But beware: they run narrow. If you have a wide foot, look elsewhere.



Finding comfortable, stylish shoes CAN be a challenge, particularly if you have a hard-to-fit size. But it’s not impossible, particularly with the Internet. If all else fails, try custom made shoes. It’s the best way to get what you want.

Have other comfortable, stylish shoe brands you like? Share it with the other readers!


Diana Pemberton-SikesDiana Pemberton-Sikes is an image consultant and author of Accessory Magic, an ebook that shows women how to use accessories to define their style and slash their clothing budget. Get Accessory Magic today.

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  • Anonymous

    Reply Reply November 1, 2013

    Take a look at Tsubo.com!

  • Vicki Webber

    Reply Reply November 1, 2013

    Hi Diana,
    I love receiving your newsletter and today’s posting was of special interest.
    Like many women, I have foot issues and am able to drool over beautiful shoes but not able to happily wear them. I came across a website that your readers may enjoy: barkingdogshoes.com
    It’s been a blessing to those of us who have to dress from the feet up!
    Kind regards,
    Vicki Webber

    • Diana

      Reply Reply November 2, 2013

      Thanks, Vicki!

  • Alina

    Reply Reply November 3, 2013

    You have no idea how long I’ve been waiting for an article like this!
    I’m only 30 and suffered a spine injury. I simply cannot wear ANY heels.
    And while it’s been relatively easy to find flats that are stylish enough for work, it’s very difficult to find fashion boots, sandals or anything flat suitable for an event.
    Please, please write an article about flat shoes for special events, that still say young.
    Thank you.

    • Diana

      Reply Reply November 3, 2013

      Hi Alina – so glad I could help! Yes, it CAN be a challenge to find fashionable, comfortable shoes if you’ve sustained an injury, have a medical condition, hate heels, etc. I will definitely keep the “Flat Shoes for Special Events” article idea in mind. Thanks for your input!

  • S

    Reply Reply November 4, 2013

    Thank you for posting this article. I will put the information to good use, especially for shoes to be worn during working hours. My poor feet thank you.

    • Diana

      Reply Reply November 5, 2013

      You’re welcome! Glad I could help!


  • Valeria Martin

    Reply Reply November 27, 2013

    I remember back in the late 70’s, my mother was in her early 50’s. She purchased a pair of very ugly “sensible shoes” from a specialty shoe store. They were custom-made and special order. Black oxfords with shiny “wet-look” leather, round-toed with a clunky heel. They were hideous! She still has them. If there was a nuclear apocolypse, the survivors would be cockroaches and those shoes! My friend calls them “mean teacher shoes”! I’m 52. I want to be comfortable, too. But no matronly shoes for me!

    • Diana

      Reply Reply December 1, 2013

      Hi Valeria, LOL!

      Yep, I remember those types of shoes precisely. Thank GOODNESS technology has evolved to where you can find stylish, comfortable shoes. No “old lady” styles here! 🙂

  • Julia

    Reply Reply August 17, 2014

    As someone with a large, very wide foot and a high instep, I have always found shoe shopping a chore. For readers in a similar situation in the UK I have recently discovered a brilliant range of fashion shoes at Evans clothing store, and also superbly comfy shoes made by the company Hotter, including some ‘to die for’ lace-ups with a really classy heel that will work with trousers and skirts (a rare combination that will certainly cut down shoes in a suitcase). I hope that this might help someone.

    • Diana

      Reply Reply August 18, 2014

      Hi Julia – Thanks for sharing! Appreciate it!

  • tj mizzi

    Reply Reply July 3, 2015

    Caprice (“walking on air”)- bought the first pair of red court shoes last year and got hooked!

    • Diana

      Reply Reply July 3, 2015

      TJ – yep, red shoes will do that for you! Lots of compliments and comments. Now try wearing them with red lipstick and see how many guys stop to talk to you… 😉

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