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Longman Dictionary of Contemporary English
well-heeled
adjective
EXAMPLES FROM CORPUS
▪ And well-heeled were they, what with the oil revenues and all. 33.
▪ And baseball will certainly have more critics ready to decry well-heeled owners buying pennants.
▪ It appeared to be a well-heeled golfer's dream.
▪ John, of course, had long since lost his northern accent and took delight in his appearance as the well-heeled businessman.
▪ Moreover commercial banks today mainly lend to well-heeled borrowers in their own countries.
▪ Peasants in cowboy hats have replaced well-heeled tourists beside a pool now filled only with two inches of green scum.
▪ There weren't, and still aren't, that many truly well-heeled people here.
▪ Typically, deaths in well-heeled Hampstead or Westminster were far fewer than in the hovels of Rotherhithe and the stews of Islington.
Douglas Harper's Etymology Dictionary
well-heeled

"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.

Wiktionary
well-heeled

a. rich; affluent; prosperous

WordNet
well-heeled

adj. in fortunate circumstances financially; moderately rich; "they were comfortable or even wealthy by some standards"; "easy living"; "a prosperous family"; "his family is well-situated financially"; "well-to-do members of the community" [syn: comfortable, easy, prosperous, well-fixed, well-off, well-situated, well-to-do]

Usage examples of "well-heeled".

Well-heeled Greys and meritocrats traveled from thousands of kilometers some, thousands of light yearsjust to spend several days browsing among the myriad of shops in each area.

Mexico, though pro-Allies, permitted a few well-heeled SinoInd refugees to take refuge in the State of Nayarit in June before she identified at least one case of plague among them.

When some well-heeled Asian men come to the States, they leave their wives at home with the kiddies and in-laws.

The Merry-Go-Round catered to war-plant workers with money to spend, and to well-heeled servicemen on furlough.

More welcoming to artists, Free-Agers, the young bohemians, and the well-heeled urbanites who enjoyed them.

His widow Angélique is supposed to have made a fortune shipping off well-heeled dafties and adventurers to Exile in the Pliocene Epoch, six million years in the past.

Probably worked her ticket in the cabin crew then opted for a ground staff post as soon as she'd snared a well-heeled oil exec.

Then she could get the kind of clothes that would make her look like a well-heeled member of the horsey set, and she could visit the Kendrick stables—.

Then she could get the kind of clothes that would make her look like a well-heeled member of the horsey set, and she could visit the Kendrick stablesget a close-up look at her target and the obstacles she would be facing.

Then she could get the kind of clothes that would make her look like a well-heeled member of the horsey set, and she could visit the Kendrick stables -- get a close-up look at her target and the obstacles she would be facing.

Then she could get the kind of clothes that would make her look like a well-heeled member of the horsey set, and she could visit the Kendrick stables—.

And it was the home of many hotels that were the equal of any in Europe, like the Grand and the Broadway, where in the early 1900s well-heeled patrons could choose between a dozentypes of hydro bath, including 'Needle, Brine, Foam, Plombiere and Scotch Douche'.

The well-heeled bill-payers like the arrangement because it gives them tax writeoffs, and the ex-government types introduce them to people in power overseas, who then help the rich people get richer.