Etymology
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well-heeled (adj.)

"well-off, having much money, in good circumstances;" also "well-equipped," 1872, American English slang (originally in the "money" sense), from well (adv.) + colloquial sense of heeled. "[A]pplied to a player at cards who has a good hand, to a person who possesses plenty of money, or to a man who is well armed" [Century Dictionary]. From 1817 in a literal sense, in reference to shoes.

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Definitions of well-heeled

well-heeled (adj.)
in fortunate circumstances financially; moderately rich;
Synonyms: comfortable / easy / prosperous / well-fixed / well-off / well-situated / well-to-do
From wordnet.princeton.edu