[masraum]

Leather shoes are going to wrinkle. There's no getting around it (other than not wearing them).

I understand that cordovan (the horse-based "leather" [not really tanned hide], not the color) doesn't wrinkle, but rolls.

darker toes is a thing, so that's not a problem either.

When leather is finished, putting a conditioner on it won't normally change the color. If you removed the finish and then put a conditioner on the leather, then you almost can't stop the color from changing. I suppose it's possible that there's some sort of conditioner that doesn't, but I've never seen it.

Those look fine to me.

I had a pair of nice-ish black penny loafers when I was in college. i eventually started wearing them for work at the grocery store. They got completely soaked in rain several times, the finish was wearing off, etc.... I took them to a shoe repair place and for something like $20, I got back a pair of shoes with new soles and completely refinished (glossy black). The shaping of the upper leather was still there, but I was actually happy about that as they were "broken in" and extremely comfortable.