You may wear one pair of shoes...

[CardiCorgi]

What are they?
Indoor slippers and wellies are allowed as additional items.

The back story, I have plantar fasciitis and tendinitis which means custom insoles. For the past year I have worn white Converse with said insoles, but they don’t really go well with my winter clothes. I can afford another pair of the insoles and was thinking of asking if they can be put into my Chelsea boots.
If you had only one pair of shoes to wear this winter, what would they be?

Thanks everyone, definitely food for thought. I haven’t worn DMs since I was a student, but I’ll check them out especially if there are some slightly less clumpy options.
If I only had aesthetics to worry about I would wear the lovely oxblood chelsea boots I bought last winter.

@MikeUniformMike the physio thinks that two months of bare feet on hardwood floors when everything was shut down earlier this year may actually be the problem. I now have ugly but supportive slippers. The tendon on the other leg is a sports injury and my running shoes also have orthotics with a slightly different shape to my everyday shoes.

It’s a good point about the Converse. The orthotic man did rip out the insides and build in the new soles, but I may need something with more support generally.

I don't know if DM still do the kensington range, but I have the Emmelines. They are less clumpy than normal DMs and you could probably get them on ebay. Another similar but IMO better version of DMs are Solovair. The Astronaut is a more elegant boot, but the 8 hole derby boot compares to a Pascal.

I didn't get on with DM Floras as my feel slopped about in them, even with thick socks and insoles, and the next size down was too small.

Easy; my Vans MTE high tops. That’s basically all I wear in winter anyway 😂

These

Fly Salv chelsea boots. I tried the doctor marten 2976 chelseas but they're too stiff and heavy. My Salvs are comfy and go with anything

My Mayari Birkenstock's. Comfiest things I own. I appreciate they're impractical at this time of year but keep them in mind for late spring through to early autumn. My hunter wellies are 15 years old & are still going strong, pricey but worth it. They get worn a lot in the autumn and winter between soggy school runs & dog walks.

White Adidas Stan Smiths

Or

Black chunky pull on ankle boots

My DH had awful PF after wearing converse and similar shoes even with insoles, he has switched to an ethical brand called Tropicfeel and it's really helped.

@Cocolapew

These

What brand are they?

My chelsea boots all the way

The idea of only 1 pair of shoes horrifies me, I never wear the same pair 2 days running . I thought being barefoot strengthened your feet? Anyway, try some <a class="break-all" href="https://www.google.com/url?sa=t&source=web&rct=j&url=m.youtube.com/watch%3Fv%3Dea4MF7IqILA&ved=2ahUKEwi7v_eO--bsAhV2QUEAHTCvA0wQwqsBMAB6BAgREAQ&usg=AOvVaw3tugD9hgLtiRx9qfZLCBzw" rel="nofollow" target="_blank">foot yoga, that might help.

I'm also thinking long term ditch the converse. They have no support at all. DH has orthopaedic insoles that he can move between shoes. He mainly lives in trainers or work boots though.

For me, in the winter I'd choose my knee high boots. They're comfy and practical, go with jeans and jumpers and dresses. They're probably not very fashionable, but I'm beyond the stage of giving a shit about that.

Fly London

Sorry that was to TikTak my ability to post is acting up

Sorry that was to TikTak my ability to post is acting up

Sorry that was to TikTak my posting is acting odd

Vans hi tops. Nothing like them for comfort and durability.

Sorry that was to TikTak my posting is acting odd

Fly London

A pair of Air & Grace - so beautifully comfortable! And I say this as someone with PF

A pair of Air & Grace - so beautifully comfortable!

Ffs

Rieker boots.

Rieker boots.

I have some ankle boots with heal by ugh and they are so comfortable and warm

@CountFosco my problem too. I like knee high boots with skirts and sometimes with skinny jeans (I know this is not on trend but it works for me), Chelsea boots with trousers, the collection of ballet flats that live in my office, casual plimsolls and sandals in the summer and an embarrassing number of sports shoes. In the winter it can be quite snowy here, so having indoor and outdoor shoes is popular too.