When Shoes Betray

credit: online world of wrestling

One of the great rules of fashion in the modern era is that shoes make the outfit.  That’s great for those women rocking the Jimmy Choos, but what about the rest of us?  Not everyone can (or should) run around in stilettos all the time.  Some of us can’t even manage a kitten heel.  Life happens, and our feet and knees sometimes say, “time for something comfy”.

Insofar as I’m concerned, one of the great overlooked markets in 2018 is supportive and/or orthopedic shoes that have some style to them.  I’m someone who struggles with my footwear, and I know there are a lot of women out there who do likewise.   The usual fashion advice, “Oh, you can just wear a ballet flat!” is ridiculous – ballet flats have no support at all.

There are thousand different shoe issues, and I’m not going to attempt to make specific shoe recommendations in a general article.   However, there are pathways to greater style … at least until the shoe manufacturers get a clue.

  • Find out what your rules are, and when (and if) they will change
    • Do you need a firm sole?  Ankle support?  A low heel?
    • Once you know the rules, be creative with them.  Maybe you have to have a flat shoe with ankle support that covers an orthotic insert.  Well, that could very well be a bootie, and there are cute booties to be had.  Maybe oxfords could work for you – there are cute oxfords to be had.
  • Talk to a professional – go to the store that specializes in supportive shoes, not the regular store.
    • These folks can often help you make shoes that fit the rules *really* work for you, and they know their product.  They’re also usually happy to make special orders.
    • Normal shoe-stores will be confused and just sell you anything that kind of works, and when you have a medical issue, “kind of” doesn’t cut it.
  • Create outfits around the shoe, not the other way ’round
    • If you’re stuck wearing combat boots (this happened to me) because that’s all you can find that fits the doctor’s orders (I didn’t know about step 2), you need to change your style around a bit to accommodate the combat boots.
    • This will frequently mean that you want to switch to pants or long skirts to blend your footwear in with your outfit, rather than the footwear being the star of the show.
  • Embrace attitude.
    • Sometimes you just have to Cybill Shepherd at the Oscars and wear your tennis shoes with a ballgown, chin up and smiling.
    • Cyndi’s wearing sensible shoes… she’s not free of style.  Be like Cyndi.
    • Bedazzle the darn things if it makes you smile.
  • Remember who YOU are.
    • Select shoes, when possible, that match your colors and your elements.
    • Whatever your style type is, if you’re being asked to wear shoes that bring you down, you’ll want to dial up the rest of your look.  Be you, just a little louder than you were before.

And finally – remember that your attitude is more important than what you have on your feet.

11 Comments Add yours

  1. Maeve says:

    I love this post! It also cannot be stressed enough that if you cannot WALK in your shoes, you certainly won’t be strutting your style. Nothing ruins a gorgeous outfit like the wearer in shoes she cannot walk in with confidence. Also, insoles. I have them for every pair of shoes I wear and I try on shoes with the insoles so that I can best determine the size. As for flats, DAHLINK, I’m totally rocking velvet flats this winter. Thank you Sole Society and Sam Edelman.

    PS, ASOS has fab shoes and a great return policy; nice in the wallet too.

    1. bayboxwood says:

      Oh my goodness – shoes are so frustrating. I love a tall shoe, real leather, classic, no platform for less than $300. Few and far between. I also love a great mule with a kitten heel, also for less than $300. Impossible. I have recently ordered the supplies to rebuild two pair of favorite shoes because I can’t bear to give them up, knowing they cannot be replaced.

      I shouldn’t complain, I haven’t suffered an injury that makes me hurt – but – Some of us just have giant flat peasant feet but still love quality stylish shoes. I’m the person who walks around high end shoe departments nodding in agreement when certain designers don’t offer styles except in very specific sizes, so I get the limited selection from the artistic perspective. Unfortunately the “fast fashion” and cultural influence answers have been making ridiculously styled shoes in men’s sizes. I am unable to source a reasonably priced age appropriate fashion conscious well crafted shoe in my size. And people wonder why some of us wander around in tennis shoes and riding boots 90% of the time.

      PS I don’t wear flats – I already don’t have an arch, I’d rather not grind down my ankles


      …but I could go on. And on.

  2. pukeko60 says:

    I need shoes with zero heel lift. Continually looking for non sneakers that work with that. Next shoues for work will look something like this.


    1. hearthie says:

      I like those shoes.

  3. bayboxwood says:

    Maybe we just found our thing?

    1. hearthie says:

      If you mean designing comfortable shoes with support – make that happen. Please. I have gone through this pain, my mom has gone through this pain – I know woman after woman (particularly in professional positions, where good shoes = status) that tear out their hair finding footwear.

      There IS a market, it’s just not 25yo.

  4. I like a wedge heel for a nice lift while still giving me stability.

    1. Maeve says:

      I love wedges too, as long as they’re not clunky – and you’re right that the wedge can really keep you stable. But then kitten heel slides! OMG I love shoes and could talk about them forevet

      1. Haha, me too! My dad owned a shoe shop when I was younger – it was fantastic!

      2. P.s. Just noticed we both have shoes in our gravatars, lol.

  5. Going to the Fields says:


    How did you get that picture of me from high school?

    I still wear my 25 year old Doc Martens. Occasionally. I love them. But lately I need minimal shoes. I can wear a 1.5, maybe a 2” heel but the pain in my ankles gets intense after a few hours. The way 4” heels are idolized some places…I should be doing housework in pumps? *smack* shut your mouth.

    My everyday shoes are a pair of New Balance Minimus trail runners. I don’t need heavy support, I do need to be able to move fast and light. For barn work, I have a pair of pull on neoprene Bogs. I want some Hunter boots when the Bogs go. Fashionability aside, Hunter boots are truly durable and functional.

    In my own quirky way, I make the minimalist sneakers work with long hippie skirts and wide legged jeans. I pull outfits together around colors or jewelry. So when I wear my blue and grey sneaks, I wear a similar hue of blue scarf or blue gem earrings. You can make it work and be all you (this is kind of what I was getting at when I expressed my sorta satisfaction at deciding to just embrace my quirks and be comfy and pretty in my own way, not someone else’s).

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