rakish

Etymology

rake (“man habituated to immoral conduct”) + -ish.

adj

  1. Dashingly, carelessly, or sportingly unconventional or stylish; jaunty; characterized by a devil-may-care unconventionality; having a somewhat disreputable quality or appearance.
    […] the rakish Dennis Quaid, a Houston native who is moving to Texas in a couple of years and wants it to become "the new Hollywood." 2007-06-08, Houston Chronicle
    Jarvis Cocker and Russell Brand have both found fame as rakish British iconoclasts. 2009-08-04, Dan Martin, “Jarvis Cocker writes songs for Russell Brand”, in The Guardian
    Harold Gould as Kid Twist (with a great mustache) wore the best Homburg in recent memory, and Redford always kept his fedora atilt at just the right, rakish angle. 2020-08-28, Thomas Vinciguerra, “Comfort Viewing: 3 Reasons I Love ‘The Sting’”, in The New York Times, →ISSN
  2. (dated) Like a rake; dissolute; profligate.

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