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The Collaborative International Dictionary of English v.0.48:

Pretty \Pret"ty\, a. [Compar. Prettier; superl. Prettiest.] [OE. prati, AS. pr[ae]ttig, pr[ae]tig, crafty, sly, akin to pr[ae]t, pr[ae]tt, deceit, trickery, Icel. prettugr tricky, prettr a trick; probably fr. Latin, perhaps through Celtic; cf. W. praith act, deed, practice, LL. practica execution, practice, plot. See Practice.] 1. Pleasing by delicacy or grace; attracting, but not striking or impressing; of a pleasing and attractive form a color; having slight or diminutive beauty; neat or elegant without elevation or grandeur; pleasingly, but not grandly, conceived or expressed; as, a pretty face; a pretty flower; a pretty poem. [1913 Webster] This is the prettiest lowborn lass that ever Ran on the greensward. --Shak. [1913 Webster] 2. Moderately large; considerable; as, he had saved a pretty fortune. "Wavering a pretty while." --Evelyn. [1913 Webster] 3. Affectedly nice; foppish; -- used in an ill sense. [1913 Webster] The pretty gentleman is the most complaisant in the world. --Spectator. [1913 Webster] 4. Mean; despicable; contemptible; -- used ironically; as, a pretty trick; a pretty fellow. [1913 Webster] 5. Stout; strong and brave; intrepid; valiant. [Scot.] [1913 Webster] [He] observed they were pretty men, meaning not handsome. --Sir W. Scott. [1913 Webster] Syn: Elegant; neat; fine. See Handsome. [1913 Webster]