Well-heeled is an American expression from the latter half of the 19th century for wealthy or rich and derives from the notion that wealthy people can afford good footwear that is not down at heel, which of course means exactly the opposite. There is another possibility about the origin because in the American Wild West well-heeled also meant, well-armed. This specific meaning could derive from cock fighting where fighting birds wore spurs and therefore were both well-armed and well-heeled. Quite how being well-armed could come to mean wealthy or rich is not clear because everyone in the American Wild West, rich or poor, appeared to be well-armed. That is why the footwear origin seems more plausible.