Definitions
American Heritage® Dictionary of the English Language, Fourth 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.
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.
Wiktionary
- adj. Stylish; characterized by a devil-may-care unconventionality.
GNU Webster's 1913
- adj. Dissolute; lewd; debauched.
- adj. Having a saucy appearance indicative of speed and dash.
WordNet 3.0
- 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).
Examples
“It turned out looking kind of rakish and cheerful and rather like how I like to think of myself.”
“I think it's kind of rakish--looks like he's winking.”
“My insistence that my haircuts are in some capacity 'rakish' no matter what anybody (chotbot) says.”
“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.”
“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.”
“My wife, who has impeccable taste, loves me in the top hat and commented that it was both "handsome" and "rakish" upon me.”
“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.”
The Wall Street Journal: 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.”
“The Tru 140S is a rakish, front-drive car in the Japanese/Korean "Fast and Furious" mode.”
The Wall Street Journal: 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
Lists
These user-created lists contain the word ‘rakish’.
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GRE Barrons Wordlist
A complete Barron's Wordlist for GRE preparation. Your online flashcard replacement.
abase, abash, abate, abbreviate, abdicate, aberrant, aberration, abet, abeyance, abhor, abject, abjure and 4084 more...
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GRE Study guide
Going through the Magoosh website, words I pulled from the verbal section. 2012.
magnanimous, correlate, anglicized, simulacrum, tantamount, obsequiousness, subterfuge, vehement, vociferous, benign, concomitant, veracity and 83 more...

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