It’s a mixed bag. I’ve bought expensive Allen Edmonds and had subtle fit problems that make them largely unwearable. Another pair of Allen Edmonds fit fine but got permanently stained is salty snow.
Recently the heal and sole of a $400 pair of dress boots completely disintegrated after four months of wear. (Resoled, but still.)
I guess I’m saying that the supposed long-term thriftiness of expensive shoes is often overrated.