Entry 3 senses Webster, 1913 Roguish · Rogu·ish · IPA /ˈɹoʊɡɪʃ/ 01 a. Vagrant. 1. Vagrant.[Obs.] “His roguish madness Allows itself to anything.” — Shak. 2. Resembling, or characteristic of, a rogue; knavish. 3. Pleasantly mischievous; waggish; arch. “The most bewitching leer with her eyes, the most roguish cast.” — Dryden.