Well-heeled definition

wĕlhēld
Having plenty of money; prosperous.
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(slang) Rich; prosperous.
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Origin of well-heeled

  • From cock-fighting sense, a well-heeled cock was provided with sharp spurs and could inflict maximum damage. Then it came along in American frontier slang to mean that one was well-equipped. In the modern sense, however, it means being armed with the most powerful weapon: money.

    From Wiktionary