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Definitions

American Heritage® Dictionary of the English Language, Fourth Edition

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

Century Dictionary and Cyclopedia

  1. 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.
  2. Resembling or given to the practices of a rake; given to a dissolute life; lewd; debauched.
  3. Jaunty.

Wiktionary

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

GNU Webster's 1913

  1. adj. Dissolute; lewd; debauched.
  2. adj. (Naut.) Having a saucy appearance indicative of speed and dash.

WordNet 3.0

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

Etymologies

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

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‘rakish’ has been looked up 3396 times, loved by 11 people, added to 68 lists, and has a Scrabble score of 13.