How to Choose Shoes with Style When You Have Foot Issues

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Shoes – we all have to wear them pretty much every day (very few of us can go barefoot out and about), and they impact greatly on your outfit as a whole, which is why when foot issues arise in your life (which they do for many of us as we age) your options for shoe styles diminishes greatly.

In this podcast episode (which was recorded before I decided to have bunion surgery) Jill Chivers of 16 Style Types and I discuss some aspects of how to choose shoes that don’t diminish your style quotient, whilst giving you the practical comfort required for foot issues.

What to do when you’ve got foot issues that allow you to wear the shoes that you want to wear as you need to wear a certain height heel or add an orthotic or for some other reason?

How to still look stylish when your shoe choices are limited?

Changing shoes can change whole aspects of your outfits, and for me, it has meant that I’ve had to rethink my style and how I put outfits together now that I need orthotics in my shoes as I’ve had to wear more closed high vamp shoes to fit my orthotics into.

Part of my personal style included feminine shoes (to me, this means more delicate and refined shoe), and now that I need on the whole a more practical shoe, that may not be as delicate, it’s changing the way I put my outfits together.  I’ve noticed I wear lots more jeans and leggings over this winter than skirts and dresses, as it was easier to fit orthotics into a more casual shoe.

My style had almost always included a more feminine shoe (even though I barely wear heels over a few centimetres in height), they were more delicate in the sole, and construction, a ballet flat for example.

Knowing that I can no longer rely on such a shoe (and now after my recent bunion surgery and the expectation of having a swollen foot for the next 6 months or so too and more shoe restrictions during this time while my bones and feet are healing) means that I have to rethink how I add that feminine aspect of my style into each outfit, yet manage to blend the practical needs of my feet and still feel stylish.

Finding shoes when you have foot issues but want to remain stylish
Silver FitFlop sneakers are more glam than a canvas version, and then I make sure my accessories are feminine and notice that there is also a frill detail on the cardigan that gives it a more feminine feel.

Instead, I need to ensure other aspects of my outfit are feminine, even if my feet can’t be, to ensure I still feel like me!

If you do have to wear a lace-up shoe, consider proportions, do you adjust proportions of the rest of your outfit so that it balances you and doesn’t make your legs look really short?

When wearing ankle boots with skirts and dresses – match your tights (if you’re wearing them) so you don’t notice where one thing ends and the next thing starts or keep skirt to above the knee, or choose an ankle boot in a nude shade.wearing ankle boots with skirts and dresses

How to Find Comfort Shoes That Are Still Stylish

Avoid shoes that have a really wide sole that sticks out of the side of the shoes, instead look for brands that have a wider footbed.  There is a  list of possible brands on this post about finding shoes to fit your orthotics.

Alternatively, you may just need a supportive flatter shoe style that supports your foot.

Oxfords are an option for dressier occasions and work well with trousers. Check out my tips on what to wear with them here.

Sneakers are another possibility for casual outfits, and they are right in fashion at present so there are lots of different colours and styles to choose from.

Finding shoes that work with orthotics and foot issues
These DKNY leather slip-on sneakers easily fit my orthotics.

There are lots and lots of ballet flat styles at Bared footwear (designed by a podiatrist) which have removable footbeds so that you can add in your own orthotics.  Not cheap, but worth signing up to their newsletter so you can find out when their sales are if they are outside of your budget!

Consider the level of refinement of the finish –  understanding of how a shoe can be upgraded by the finish, such as a patent leather, or a metallic, rather than if it’s in a plain matte leather or a canvas also helps to add a level of sophistication.

Finding shoes to work when you have foot issues such as needing to wear orthotics
These more casual Down to Earth ballet flats I bought in a size larger and happily fit my orthotic insoles and still work with skirts and dresses (though they do have a more casual vibe)

The thickness of the sole will also impact on the level of refinement and how dressy a shoe appears.  A thick rubber sole that sticks out the side edges of a shoe will always look more casual, than a shoe that either has a finer sole or a sole that sits within the footprint of the shoe upper.

Look for shoes with some detail to make them more dressy and interesting.  These ankle boots have an interesting detail on them.

Finding fabulous shoes when you have foot issues but want to look stylish

I purchased these in a size larger than my normal size so I could comfortably fit my orthotics inside.

How to Add Style to Your Comfortable Shoes

So you’ve found some shoes that are comfortable and practical, but let’s face it, they are dull and unstylish (or even a terrible colour for you).  Why not think about up-styling shoes like Jill does.

Sassy Feet is a book recommended by Jill on how to upstyle your shoes – this is a great option if you can’t find shoes in colours that work with your palette or are just plain boring.


Got a boring black shoe but don’t wear much black?  Why not paint your shoes and make them a colour you love?  Or alternatively, you can dye leather shoes as well (though not to as many colours).

A coloured shoe can add something interesting to your outfit too, even if it’s not hugely embellished.  Alternatively, go for a nude shoe, something that blends to your skin, so that your shoes aren’t the focus of your outfit.  They become much less obvious, so painting a black, tan, brown (or whatever colour) shoe to a colour that is your version of nude is another way to upstyle your shoes.

Further Reading

Finding Shoes for Orthotics That Are Stylish

How to Have the Perfect Wardrobe of Shoes

How to Wear Flat Shoes

How to Find the Most Comfortable Shoe

How to Choose Shoes with Style When You Have Foot Issues

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I'm not sure if it's for you but how would you feel if you learned all about the colours and styles of clothing that suit your individual personality, shape and style? Just imagine what it would be like when you can open your wardrobe and pull together fabulous outfits that make you look and feel amazing every day? If you'd like to stop wasting money on the wrong clothes and accessories plus join an amazing bunch of very special women also on their style journey - then my 7 Steps to Style program is right for you. Find out more here.

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15 Comments

  • I have to wear orthotics which are usually too wide for the shoes that fit my feet. Like a comment before…I need a very slightly wider front and a narrower back. And I need a low vamp as I have arthritis in the bone where others have bunions. Anything that goes across that is too painful. So I end up having yo wear soft ballet pumps that provide no support ( and rarely accomodate orthotics). There is nothing suitable for me so I continue to suffer with my feet and then my knees etc etc. If only there was somewhere to go to get them custom made. I would be willing to pay for comfortable stylish shoes. I’m in the UK by the way. Most orthotic shoes come in frumpy clumpy black!!! I’m a Spring so light warm colours are my go to. Try finding them in the colder months!!!

    • Lynn,
      Try Hotter shoes. They are made in the UK, and can fit an orthotic insert if you remove the liner. They have some attractive (non-frumpy) styles, a good size range, and reasonable prices.
      I’m a light spring as well, and haven’t owned black shoes in years because they don’t go with anything in my wardrobe. I have some cute maryjanes from Hotter that are a soft metallic gold, which I love!

  • Hi Imogen,
    I am having to wear comfort shoes nowadays, as came back from holiday, walking around too cities in agony, pains right up the legs. My own fault as I have flat feet and bunions due to trigger toes from childhood, a family trait. I saw an orthoeopedic sugeon some years ago, who said they were too far gone for surgery, so try to find shoes with arch support in them, rather than ortho things you put inside shoes, that move about apparently and can cause more problems. I have found that Ecco shoes made in Sweden are great, many of their styles have inbuilt arch support and look quite trendy. Merrell from US make walking boots and much more casual swede boots, short and long nowadays, which are so comfortable with arch support too. Fortunately we are mostly more casual nowadays anyway and these styles look fine. I was told in local shop here in UK that they have loads of women in their thirties now coming in, not because they have problems, but they are so into the comfort thing and they look so wearable!

  • I’m delighted to have found Cosyfeet, a maker of shoes and boots specially designed for people with foot problems. I used a pair of their soft, lightweight lace up canvas shoes all summer, and am getting a couple of pairs of lace up ankle boots designed for people with bunions. They look perfectly ok, and are sooo comfortable! Highly recommended!

  • I have really liked Clarks! I know they are really kind of preppy looking but there are some styles that look good. I’ve dealt with this for years. Try the blog Barking Dog Shoes blog.

  • Hi Imogen,
    I have very tricky feet, bunions and flat feet due to trigger toes from childhood and the surgeon said too bad for surgery, they have gone too far. I cannot wear ortho things in the shoes as they rub my feet raw underneath, I have very thin, fair Irish skin and he did not like the idea of them anyway, as they rarely fit properly inside shoes. Instead, I was advised to find shoes with inbuilt arch support, such as Merrell walking boots – they also make more casual styles of everyday boots. Fortunately, the world has gone more casual in dress and I no longer go to an office to work. I have found some styles of Ecco have the arch support too and some better specialist shoe shops are great at helping you. I have come to the conclusion that I cannot wear ordinary fashion shoes anymore, after walking around Europe on holiday this summer, I came back nearly crippled with swollen ankles, pain throughout the length of my legs and lower back. As someone who likes to go hillwalking and doesn’t drive, I walk everywhere, despite flat feet, so have to be sensible from now on. Good luck with your recovery!

  • This year, due to a knee injury, I have transitioned from heels to flats, and to wearing orthotics with ALL my shoes. My podiatrist was really helpful & also made a half-orthotic in a nude colour for me to wear with dress flats. She also encouraged me to bring in a suitcase of shoes for her to go through & explained how to wear them with the half-orthotic, and which styles provided the best foot support.

    I sing professionally, on occasion, so wear a lot of formal/evening dresses, and this transition hasn’t been easy!

    Flat shoes which accommodate HALF-orthotics and work well with dresses & skirts include:

    WINTER SKIRTS & DRESSES:

    Casual:

    Flat almond-toe or round-toe leather knee-high boots, with a thin sole & very well fitted.

    Business:

    Flat, almond-toe over-knee boots in a matt microsuede, with a very thin sole, fitted to within an inch of their life! (I took them in myself on the sewing machine, after discussions with my cobbler). The top of the boots dissappears underneath the hem of my skirt, so it creates a slim/elongating line. The boots look delicate/feminine because they aren’t chunky, and being so well-fitted they hold my half-orthotic better than any other shoe I own.

    Evening/dressy:

    Very low heel, pointed-toe over-knee boots in crushed velvet , with a very thin sole and bling/embellished heel detail.

    SUMMER SKIRTS & DRESSES:

    Casual:

    Cute, metallic sneakers in nude colours (eg: pink/silver/rose gold).

    Flat, strappy sandals in nude colours. Unfortunately I can’t wear my orthotics with these, as they don’t stay in place & can be seen, but at least the shoes are flat!

    Or a more casual version of the next shoes…

    Business:

    Pointed-toe d’orsay flats, with a high ankle strap. Yes, I wear my half-orthotics with these, even though the centre of the foot is exposed. Because they are nude & the heel hides a large portion of the orthotic, the only part you can see is under the arch of the foot – but who cares! You’d really have to be paying a lot of attention to my arches to notice. And besides, I’m comfortable & supported.

    Evening/dressy:

    Pointed-toe D’Orsay flats, with ankle straps, or T-bars, in nude colour with loads of embellishment – I have found bridal flats a great option (satin, embellished, bling, strappy ties, sequins etc.)

    Flat, metallic sandals with loads of bling (embellished T-bars, or straps which wind around my ankles like bangles – jewellery for my legs!) – again, bridal sandals are a great option. Ditto: unfortunately I can’t wear my orthotics with these, as they don’t stay in place & can be seen, but at least the shoes are flat!

    Sorry for the long post – lots to share. Hoping this helps some of you in the transition process!

  • I use Hotter, Ecco (better sizing for me) and Clarks. Problem is that I can’t usually buy a size bigger to fit orthotics as my feet barely fit into the largest sizes (tall with big and wide feet). I have a very high instep and need a very deep shoe front. I hope to use this post to find some comfortable dressier and more feminine shoes.
    Ironically I’m in a moonboot after fracturing the base of my 5th metatarsal – and I have to wear a higher heel than usual to balance up my hips

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