As I reached my shoe 'social' high point years' ago, I no longer buy shoes as have over-supply for my current needs!
I have a cull to do, at which time, those I no longer wear, or just plain don't want anymore, will go to Lifeline. My shoes are always kept in their boxes, so they in excellent condition.
My oldest pair are 'black sparkly' evening shoes, which I bought in 1969, for the huge sum of $19.95, when my wage was $35.90 gross a week! My daughter now wears them!
My second oldest pair, 35 yo, which I wear as a 'dress shoe' is my much loved pair of Tan, R.M. Williams' low-heeled boot. The're just soooo comfy, & look fabulous with my jeans! I've also a black pair low-heeled & Cuban heeled black pair. All these three are 'dress' wear.
I've separate Riding Boots, as they tend to get messy for many reasons' around horses'!