Trainers all the time - not my natural style

[Problemhooves]

I have problem hooves (hence the username).

It seems that the only footwear I can wear which doesn't bother them* is trainers. Not sleek trainers either, big, chunky walking trainers. They really aren't my style but needs must.

Can anyone help me with styling them or even just help me feel better about wearing them with my usual clothes? I normally wear pointed flats, low heels, I'm adjacent boots but a bit less chunky, or not chunky loafers.

I wear a lot of wide leg trousers, shirt dresses, maxi skirts with a jumper (sort of 90s style)

*when I say "bother them" I mean cause intense pain for days - not just a bit uncomfortable

What kind of problems (sorry Im a podiatrist so curious) don't answer if you don't want to.
Bunions? Hammer toes, high arched feet, extra wide or narrow, other? If I know I might be able to help.

No problem - high arches and plantar faciitis

I've been in the same boat since mid 20's, it is hard!

I wear Air Max 90s pretty much exclusively because they're deep enough to fit my orthotic insoles but still look OK-ish. Birkenstocks in summer. If you need insoles and you can get away with a half-length orthotic you can fit it into loafers and expand the options that way.

It was alright the last ten years but I feel like fashion has swung back to thinner shoes now (Gazelles, ballet flats etc) which is unfortunate!

Yes high arched feet are a sod to get shoes for and boots even worse.
Im having cortisone injections into my big toes on Monday because the arthritis pain in them has hit the roof.
Im wearing chunky zip + lace up boots that I can get my feet into without killing my toes and adjust for comfort, Halloween llama leggings because I love Halloween and a very nice longer length black hoodie from Very. I think the orange trousers take the attention away from my orthopaedic style boots and look quite nice.
Quite honestly I refuse to suffer from foot pain. If I had plantar fasciitis I'd get a cortisone injection. Otherwise it can just go on for months on end.
Alternatively wide leg long trousers that cover most of the shorts, Adidas or the like.

I feel your pain! I love the look of gazelle type trainers but no good <sigh>

PS: just noticed typos in op. Hope it makes sense! Should've said "DM adjacent boots". Stupid autocorrect

Thank you. Maybe I'll do that.

Love the leggings!