Comfortable winter footwear with jeans.

[HierarchyOfMugs]

I'm trying to put together a few outfits for autumn & winter but I'm a bit stuck when it comes to shoes. I'll be wearing jeans when it gets cold, but don't know what shoes/boots I want when it's too cold & wet for trainers.
What boots would you wear with boyfriend/baggy jeans? They need to be flat & comfortable as I'm developing plantar fascitis. ☹️
I'm already sorted for bootcuts with long flat lace-up boots.

I wear goodwinsmith.co.uk/products/ladies-gs-cassia-work-boot

Surely what works for bootcut will work for baggy as well?
I figure that a pair of chelsea boots and a pair of DM type boots will see me through winter.
(obv a pair of wellies for dog walking too!)😃

@henlake7 do you think? I'm rubbish at this. I've taken some photos of various jeans with my usual long boots. I've rolled one leg up because I can't tell which looks better. None of them look great to me, tbh.

I should have said I can't wear Chelsea boots due to my freakily narrow feet.

Bootcuts. This is what I've worn in previous years.

Boyfriend. This looks odd to me with long boots

Baggy.

501s

@MikeRafone they look nice but they don't come in my size, unfortunately.

I have DM’s and winter converse high tops (leather outer with a warm inside).

I'd roll the jeans up a bit more and I think they'd look fine - I normally have the jeans nestled at the top of the boots. A more chunky boot would also look good - I've just bought some brown ones from M&S although they're not mega chunky. I generally prefer brown boats with jeans although I have no idea why!

@mynameiscalypso these are knee high boots, would rolling the jeans up more still work? Or do I need ankle boots?
If I wear loose jeans & chunky boots will I look like a builder? 😆

Ah, I thought they were ankle boots. I definitely think it's a better look with ankle boots personally. I balance out the shape by having a bit more of a fitted top.

What about these? Would they look ok?

Oh yes, I love those! They're similar (but nicer) to the shoes I bought this morning.

Yes, best photo so far 😀

Thanks everyone! I'll order the Next boots.