Definitions

from The American Heritage® Dictionary of the English Language, 5th Edition.

  • adjective Sexually promiscuous. Used of a woman.

from Wiktionary, Creative Commons Attribution/Share-Alike License.

  • adjective Easily defeated; a pushover.
  • adjective Of lax morals; sluttish.

Etymologies

from The American Heritage® Dictionary of the English Language, 4th Edition

[From roundheels, a boxer who is easy to knock out, from the image of a promiscuous woman frequently being on her back.]

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Examples

  • Albeit round-heeled, wading into the swamps, beaches and velour mouse-ears of Florida.

    Archive 2008-01-01 2008

  • Women typically fell into one of two categories: attractive, round-heeled, eager wenches who fawned over his looks and fell into his bed at the snap of his fingers, and the rest of them, whom he barely noticed.

    Shameless KAREN ROBARDS 2010

  • Women typically fell into one of two categories: attractive, round-heeled, eager wenches who fawned over his looks and fell into his bed at the snap of his fingers, and the rest of them, whom he barely noticed.

    Shameless KAREN ROBARDS 2010

  • Well, I hadn't thought of it that way exactly, but .. yeah, now that you mention it, that's exactly what McCain is: the round-heeled mistress to this whole big Kleptocracy that has been in office for the past eight years.

    McCain's Embattled Campaign Manager Skips Lunch With Reporters 2009

  • So now, shorn of all the technicalities, the Supreme Court gets a chance to say whether it means what it's always said, or whether it wants to endorse the fast and flashy round-heeled patent system we were running during the boom times.

    Eben Moglen: An Important Patent Law Precedent Approaches 2009

  • There are thoroughly convincing round-heeled debs, dissolute preppies, money-hungry upper-East-Side divorcees, and other more or less obnoxious types in the novels.

    Ben Gates Is Hot Ed Gorman 2009

  • Amanda Watkins, who plays the round-heeled chorus girl with the Judy Holliday accent who gets to sing "Always True to You in My Fashion," is seriously sexy.

    Recipe for a Hit: Just Add Waters 2008

  • Back down here on earth, while it was damn silly for Soviet aesthetes to go into a poetic swoon over farm equipment, somehow, the act of going collectively round-heeled over electronic appliances (including jealous rages that lead to homicidal outbursts) doesn't seem like the sort of communal practices that will allow an empire to endure for long.

    Prisoners of Envy: Wal*Mart Nihilism Versus the Punk Rock of Blogging 2006

  • On interview shows and in congressional testimony Michael Powell became the face of what William Safire, in The New York Times, called the "round-heeled FCC."

    The Age of Murdoch 2003

  • On interview shows and in congressional testimony Michael Powell became the face of what William Safire, in The New York Times, called the "round-heeled FCC."

    The Age of Murdoch 2003

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