Etymology
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rakish (adj.)

1706, of persons, also style or appearance, carriage, etc., "debauched, disreputable, having the manners or appearance of a libertine or idle and dissolute person," from rake (n.2) + -ish. Related: Rakishly; rakishness.

The meaning "smart, jaunty, dashing" (1824), at first of ships, is said to be a different word, from nautical rake "slant, slope" (1620s), used of the projection of the upper part of a ship's hull at stem and stern beyond the extremities of the keel, later especially in reference to any deviation from the vertical in a ship's masts. That word is of uncertain origin, perhaps from Scandinavian (compare 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].

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Definitions of rakish

rakish (adj.)
marked by up-to-dateness in dress and manners;
rakish (adj.)
marked by a carefree unconventionality or disreputableness; "a cocktail party given by some...raffish bachelors"- Crary Moore;
Synonyms: devil-may-care / raffish
From wordnet.princeton.edu

Dictionary entries near rakish

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RAM