Q From Michael McKinney: Any interesting tidbits about the expression well heeled?
A Well-heeled never had anything to do with people being well shod (so it has no link with down at heel). The original expression came from cock-fighting, and meant to provide one’s bird with good, sharp spurs (considered, it would seem, as a kind of artificial heel) that would inflict the most damage. It was taken over into American usage in frontier days to mean that one was likewise carrying a weapon, but in the more modern sense of a gun (the first recorded use is from a story of Mark Twain’s dated 1866). Only later did it transfer its meaning to being armed with a more powerful weapon still: money.