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?

Doc Martens boots

DMs oxblood chelsea boots

I really want some Chelsea boots! I think based on what I currently have, I'd choose my black, mid-calf Fly London boots. They are incredibly comfortable and just about work with smart casual for work as wellas casual for at home.

Sympathies on the PF - I had it for 2 years. All gone now, thankfully.

These Camper Peu Tourings: www.camper.com/en_GB/women/shoes/peu/camper-peu-K400374-007

Only downside, poor sole grip (ground side, not foot side). Otherwise they are the perfect everyday shoe (NB: I also have plantar fasciitis from time-to-time).

I have them in black, white sole.

Another vote for DMs. They go with everything and are so light and comfortable (if they fit properly). They're also good for walking on ice/snow if we get a cold winter!

I'm thinking of getting another pair of DMs. They go with anything

I’ve got some Ugg Chelsea boots (they look like normal leather Chelsea boots not like the sheepskin ugg boots!) they’re wool lined and so cosy, plus nice and wide for my big feet

DM boots. I'm eyeing up the chelsea ones at the moment

The nicest shoes I could find made by rocket dog would be my choice. They're so comfortable I can even wear their heels all day without getting sore feet.

Blundstone boots.
I wear them 90% of the time anyway.

Moshulu Nightjar Calf length boots - so comfy & practical:

www.moshulu.co.uk/product/nightjar-wedge-mid-length-leather-boots-1307#?variant=186

Ankle boots with block heels.

You can get custom insoles for plantar fasciitis that you just move between shoes.

No need to be stuck with one pair only ;-)

Converse may not be helping as they are flat and heavy. Shoes with more support generally will help you.

When I had this problem I found trainers to be the most comfortable. A good sports Shop will help you choose the right ones for your issues.

Grenson Nanettes in black.

these

My DMs, the purple ones if I’m grumpy as they cheer me up, Chelsea boots if I have to walk a lot, velvet ones if it’s dry and my long embroidered ones on the rare occasion when I wear a skirt!

DMs, probably Chelsea Boot style.

Fitflop ankle boots. They are so comfortable and the leather is nice and soft, easy to break in. Wear with almost everything, skirt, rolled up jeans, dress. I wear mine almost every day.

Not read the replies but I'd bin the Converse as they provide no support. Might be ok with the orthotics though.

put into my Chelsea boots. Lovely as chelsea boots are, they are often not a good fit. I'd get a pair of lace up shoes or ankle boots that fit properly with the orthotics in them.

Chelsea boots

Art company Skylines. Not to everyone's taste but they've been my absolute work horse shoes for over 18 years and I'm only on my second pair. I wear these more than any other shoes I've ever owned

@CardiCorgi, if you were wearing the plimsolls you mentioned in the OP a lot, they may have caused the plantar fascitis.

@DelphineWalsh, they are not my cup of tea but the Art Company has some really cool shoes and boots. Thanks.

these? www.the-art-company.com/en/unisex-shoes-toronto-grass-leather-carmin-1412.html