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?

I can also get my fat feet plus orthotics into Fairfax and Favor heeled Regina boots. They cost a bomb but are leather lined and, with an annual resoling and reheeling, still look good 3 years in. You can get the same boot in lots of colours and at a much lower price from House of Bruar. I wear mine with skirts and with skinny jeans.

Thanks Op, I'd live in suede boots if I could but I'm in Asia at the moment and it's a tad too hot for then in the day, so trainers it is. I do have a lovely pair from Carvela from their comfort range, mid heel, soft sole made for comfort.

Adidas superstars. Very comfortable for long walks, waterproof and go with anything.

I'd like a brand new pair of my favourite Italian ankle boots, or someone who can resole the ones I have. They are so comfortable, go with everything... and they are nearing their end.