In short, to be well-heeled is to literally be well to do enough to wear a pair of expensive high heels or, figuratively speaking, to be rich, wealthy, affluent, well off, well provided and well to do in general.
Here are media examples:
1. 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.
- Well Heeled, WorldWideWords.com, October 3, 1998.
2. The term “well-heeled” is an American expression that dates back to the mid-1800s. As town cobblers made and repaired shoes, those who could afford the repair service and/or new shoes were considered well-heeled. Well-heeled is the opposite of the American expression “down at the heels” used in the seventeenth century. The heels on the shoes of the poor were often worn down and differed from those of the rich who were able to maintain their shoes or afford new shoes, while the poor could not.
Many people in the United States in the early 1800s went without shoes during the spring and summer and many others wore shoes only on special occasions such as church or school. Some children never even owned shoes until they were teenagers. By the mid-1800s shoe making became more industrialized and wearing shoes year round became more common.
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