Some drivers with a minimal, sectioned sole would probably work great. I have a pair with a latex rubber sole that is very soft and extremely quiet.

Go with something like this and treat it with some mink oil (waterproofing for dress leather). https://www.johnstonmurphy.com/xc-flex-connelly-shearling-boot/02005683-080-M.html

Officine Creative has some similar, but you’ll be paying more fore them.

Width is more important than length as long as your toe isn’t making contact with the front, and you aren’t tripping over them like clown shoes. Looking at how much gap you have in those laces, if they are staying on your feet and not flopping around, you are good.

Worth a pin IMO. That and some explanations of care products could be a go to answer to a lot of posts here.

Rubber sole chukkas are not a dress shoe but would probably look out of place with sweatpants. They go great with jeans, and can pass for office casual.

Moisture damage.

Go talk to the folks at your local food bank. they should be able to point you towards whatever programs in your area supply shoe and clothing donations. You should be able to get a new, unworn pair that way.

Are you looking specifically for that lightweight knit upper? I can recommend a few I know in that same style but with a leather or thicker material upper, or a few with that same material in a different style (still slip on, but with false laces to look like a sneaker or oxford).

It’s probably a broken air pocket in the interior of the outsole making the squeeking sound. It’s a somewhat common thing in air cushioned outsoles. I have a pair of sneakers that do this, and it can be annoying sounding like a dogs chew toy. I haven’t experimented with it yet myself, but I think if you were able to open up the hole/punch a new one into the offending air chamber, you could provide some more release and stop them from making that sound.

Look to be very good quality. I’d recommend storing them with shoe trees to maintain the shape.

Maybe thinking something along the lines of this? https://www.themanual.com/fashion/jeans-in-freezer-freezing-denim-myth/

There are a few things this could be, and they have different solutions. So follow up questions:

Where on the heel is it wearing most (inside, outside, back)?

What material is it (traditional rubber, crepe, eva foam, leather)?

Do you drive a lot?

The cheap dress socks are probably cotton polyester blend, and a big factor in your feet ending up like that. Switch to 100% wool. I know it sounds counterintuitive, but wool breathes really well and wicks moisture. I had a lot of problems with foot sweat until I switched out all of my socks for wool.

That color change is permanent. Suede does not like moisture. Your best advice is to pre-treat your suede shoes/boots with waterproofing before you wear them.

https://www.johnstonmurphy.com/shoe-wash/09300461.html

This stuff is my go-to for any stains on a white sole. Works way better than any of the home brew treatments.

A lot of the premium brands will have clearance prices for last years model at or under your price point. I don’t know about the UK, but in the US a lot of brands have “factory” or “outlet” stores that sell cheaper versions and also have large sections of old product at massively reduced prices (I regularly find $300-400 designer shoes for $70-120 this way).

If you want to preserve a crepe sole; don’t drive in them, don’t walk on hot black top with them, and don’t drag your feet. That’s about all you can do. These ones at least can be resoled with leather after you wear them out (most cobblers won’t do crepe).

Too loose. Your foot is moving around in them, and the friction is causing blisters. Shoes should be snug, not roomy.

Also keep in mind that a mens medium width is a womens wide, so if you are getting a shoe in womens size for someone who fits a 9.5 mens you should go 2 sizes up or get them in wide.