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rakish1

[rey-kish] /ˈreɪ kɪʃ/
adjective
1.
like a rake; dissolute:
rakish behavior.
Origin
1700-1710
1700-10; rake2 + -ish1
Related forms
rakishly, adverb
rakishness, noun
Dictionary.com Unabridged
Based on the Random House Dictionary, © Random House, Inc. 2014.
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British Dictionary definitions for rakishness

rakish1

/ˈreɪkɪʃ/
adjective
1.
dissolute; profligate
Derived Forms
rakishly, adverb
rakishness, noun
Word Origin
C18: from rake² + -ish

rakish2

/ˈreɪkɪʃ/
adjective
1.
dashing; jaunty: a hat set at a rakish angle
2.
(nautical) (of a ship or boat) having lines suggestive of speed
Word Origin
C19: probably from rake³ (sense 1), with reference to the sloping masts of pirate ships
Collins English Dictionary - Complete & Unabridged 2012 Digital Edition
© William Collins Sons & Co. Ltd. 1979, 1986 © HarperCollins
Publishers 1998, 2000, 2003, 2005, 2006, 2007, 2009, 2012
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Word Origin and History for rakishness

rakish

adj.

1706, "debauched, disreputable," from rake (n.2) + -ish. Related: Rakishly; rakishness.

The meaning "smart, jaunty, dashing" (1824) is said to be a different word, probably from rake "slant, slope" (1620s), used especially in reference to a ship's hull or sails, of uncertain origin, perhaps from Scandinavian (cf. Old Swedish raka "project, reach;" Danish rage "protrude, project") related to Old English reccan "stretch." "The piratical craft of former times were distinguished for their rakish build" [Century Dictionary].

Online Etymology Dictionary, © 2010 Douglas Harper
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17
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