slyboots

• sly-boot
• sly-boots
• slyboot

sly +‎ boots

slyboots (plural slyboots)

1. (chiefly Britain) A person who is clever or shrewd, especially one who is stealthy, manipulative, and rather charming.
   • 1838 July 24​, Ralph Waldo Emerson, “Literary Ethics. An Oration Delivered before the Literary Societies of Dartmouth College, July 24, 1838”, in J[ames] E[lliot] Cabot, editor, Nature, Addresses, and Lectures (Emerson’s Complete Works; I), Riverside edition, London: The Waverley Book Company, published 1883, →OCLC, page 166:

     But Truth is such a flyaway, such a slyboots, so untransportable and unbarrelable a commodity, that it is as bad to catch as light.

   • 1857–1859, W[illiam] M[akepeace] Thackeray, “Troubles and Consolations”, in The Virginians. A Tale of the Last Century, volume II, London: Bradbury & Evans, […], published 1859, →OCLC, page 283:

     "Oh, you sly-boots!" says the Countess. "Guess you come after the old lady's money!"

   • 1922 February, James Joyce, “[Episode 15]”, in Ulysses, Paris: Shakespeare and Company, […], →OCLC:

     You're such a slyboots, old cocky. I could kiss you.

   • 2004, Umberto Eco, Geoffrey Brock, transl., The Mysterious Flame of Queen Loana, New York, N.Y.: Harvest/Harcourt, page 54:

     This slyboots took me for a ton of money, made me do whatever she wanted.

• artful dodger, con artist, operator, rogue