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, Ralph Waldo Emerson, Literary Ethics - an Oration delivered before the Literary Societies of Dartmouth College, July 24, 1838
   • 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 1061908157, 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 560090630:

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

   • 2004, Umberto Eco, The Mysterious Flame of Queen Loana, trans. Geoffrey Brock, Harvest/Harcourt (New York), p. 54:

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

• artful dodger, con artist, operator, rogue