be well-heeled

To be particularly wealthy. A: "I heard that Tom lost his job." B: "Yeah, but his family is quite well-heeled—he'll be fine." They're going to Malaysia for their summer vacation? Gosh, it must be nice being so well-heeled. Because my grandparents are well-heeled, they very graciously agreed to pay for my education.

well-heeled, to be

To be prosperous. This late nineteenth-century Americanism presumably refers to a well-off person who is not down at the heels but is well shod. “To travel long out West, a man must be, in the local phrase, ‘well heeled,’” wrote W. Beadle (The Undeveloped West, 1873).