If you're talking about dress shoes you don't expect the soles to last especially longer than those on cheap dress shoes. With the higher quality ones you can, and it is worth it to, resole and remanufacture them multiple times. My best dress shoes are ten years old, have been redone once, and are likely to last another 20 years.

That said, I don't think this accounts for rich people having more money

That's why most people don't take their economic advice from works of fiction.

Chris Rock had a character on SNL. He was a militant black panther giving stock advice. It was great.

Does anyone have the name or any clips?

It sounds like you're comparing some kind of dress shoe to sneakers. For it to be an accurate comparison, you'd need to compare the custom dress shoes to cheap dress shoes. Also, it's pretty hard to beat the cost of sneakers for footwear if you have no need for dressier shoes.

I've done something similar, but with different results...

I wear down heels very fast, and used to get through mass-produced shoes with moulded soles far too quickly. It annoyed me hugely that I had to throw away a pair of shoes whose uppers were in perfect condition, but whose soles couldn't be replaced.

In the end, I bought a pair of decent leather-soled shoes for $350 and get them heeled regularly; that was 7 years ago, they're still going strong, and I estimate that they've saved me a ton of money.

And as a "third way", I've kept my eyes open in thrift (UK = charity) shops, and have managed to get excellent, repairable footwear for next to nothing. My current pair of oxblood brogues by Allen Edmonds cost me $25, has been going for 5 years now, and barring accidents will last me until I'm well past retirement...

That's a little extreme - a fairer comparison would be Allen Edmonds vs. a budget dress shoe.

If you want to beat sneakers in terms of price, switch to work boots like Red Wings or Chippewa.

1 - good shoes outlast the soles, and can be resoled

2 - the modern world has dramatically increased the price-per-quality on the cheap stuff, shrinking the gap

What kind of quality shoes? Good dress-y shoes can be resoled so they should last more than 4 years.

I own two pairs of sneaker-y leather shoes that look like Timberlands from the 1980s, both made by a cobbler back in Italy who has since retired. They are 6 and 8 years old respectively, and only needed resoling twice.