Well-heeled

Well-heeled: having plenty of money. From http://www.jewishworldreview.com/0304/dictionary_men030104.asp:

There is some dispute over the origin of "well-heeled,'' which means "wealthy.'' We know it originated in the United States in the late 1800s, but its derivation is unclear. One popular explanation is that wealthy people have plenty of money to see that their shoes are always stylish and in good repair, not worn down at the heels; hence they are literally "well-heeled.'' 

The other explanation for "well-heeled'' is somewhat more complicated. In the late 1800s, "well-heeled'' was also used to mean "adequately armed with weapons.'' As the story goes, this use of the term derived from the practice of equipping fighting gamecocks with steel spurs. Eventually, according to this theory, the sense of "well-heeled'' meaning "wealthy'' evolved out of this "well-armed'' sense. 

The theory seems plausible, since wealth can indeed be a powerful weapon, and it's true that the "armed'' sense of "well-heeled'' is attested some ten years earlier than the "wealthy'' sense. But it's also possible that the two meanings developed fairly simultaneously, independent of each other. Without more clear-cut evidence, we can't say for sure whether the first person to use "well-heeled'' to mean "wealthy'' was drawing the imagery from shoes, or from guns!

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