$50/$500 is a 10%/year yield, which is hard come by in any guaranteed investment. The Crocs will likely have no retained value, while the $500 shoes may be worth something after 10 years.
However, that ignores the cost of maintaining a nice pair of shoes (both money and time) as one needs to clean, polish, and resole every so often.
You might want shoes in two or three colors/styles, which would make the Crocs last 2-3x longer, same for the other shoes, but are you really going to want the same expensive shoes in 30 years?
I think the higher end stuff that retains value and requires less maintenance might be a better example, like if someone is good at buying watches they could get a Rolex that appreciates in value and ends up costing them nothing vs a series of cheaper watches. Or compare to a $500 Apple Watch you replace every couple years. I don’t wear watches, though, and I’m not good at buying or selling them.
Really, I think there are some expensive, durable goods that last longer and are cheaper you might think, but still more expensive once you take into account the maintenance and time value of money. But nice stuff is nice to have, and it’s helpful that you don’t have to replace it so often.