Definitions

from The American Heritage® Dictionary of the English Language, 4th Edition

  • adj. Nautical Having a trim, streamlined appearance: "We were schooner-rigged and rakish, with a long and lissome hull” ( John Masefield).
  • adj. Dashingly or sportingly stylish; jaunty.
  • adj. Of the character of a rake; dissolute.

from Wiktionary, Creative Commons Attribution/Share-Alike License

  • adj. dashingly, carelessly, or sportingly unconventional or stylish; jaunty; characterized by a devil-may-care unconventionality; having a somewhat disreputable quality or appearance.
  • adj. like a rake; dissolute; profligate

from the GNU version of the Collaborative International Dictionary of English

  • adj. Dissolute; lewd; debauched.
  • adj. Having a saucy appearance indicative of speed and dash.

from The Century Dictionary and Cyclopedia

  • Nautical, having an unusual amount of rake or inclination of the masts, as a vessel. The piratical craft of former times were distinguished for their rakish build.
  • Resembling or given to the practices of a rake; given to a dissolute life; lewd; debauched.
  • Jaunty.

from WordNet 3.0 Copyright 2006 by Princeton University. All rights reserved.

  • adj. marked by a carefree unconventionality or disreputableness
  • adj. marked by up-to-dateness in dress and manners

Etymologies

Probably from rake3 (from the raking masts of pirate ships).
(American Heritage® Dictionary of the English Language, Fourth Edition)

Examples

  • It turned out looking kind of rakish and cheerful and rather like how I like to think of myself.

    Hip Op minus four days

  • I think it's kind of rakish--looks like he's winking.

    What I cooked last night.

  • My insistence that my haircuts are in some capacity 'rakish' no matter what anybody (chotbot) says.

    robotsarered Diary Entry

  • She laughed, standing as cool as you please, very grateful to the eye in tussore coat and skirt, with open-necked blouse, and some kind of rakish hat displaying her thick auburn hair in defiance of the fashion which decreed concealment even of eyebrows with flower-pot head gear.

    The Mountebank

  • It's not that hard to imagine him in the part -- Reynolds had the kind of rakish charm that Harrison Ford ultimately brought to the role.

    Forbes.com: News

  • My wife, who has impeccable taste, loves me in the top hat and commented that it was both "handsome" and "rakish" upon me.

    Time to Top Up?

  • The exterior styling changes are so subtle as to be subliminal: some character lines here and there, a narrowed stare from upswept headlamps, a slightly more rakish windshield.

    Honda's Sporty New Civic, Heavy on the 'Ick'

  • Honda The exterior styling changes are so subtle as to be subliminal: some character lines here and there, a narrowed stare from upswept headlamps, a slightly more rakish windshield.

    A Giant Stumbles

  • The Tru 140S is a rakish, front-drive car in the Japanese/Korean "Fast and Furious" mode.

    Which Car Fantasies Should Come to Life?

  • Yet it also had the Hellfire Club, a place frequented by nobles and politicians to carry out rakish and immoral acts.

    Japanese Gropers: Molestation Hits a New Low « Colleen Anderson

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