- like a rake; dissolute: rakish behavior.
- smart; jaunty; dashing: a hat worn at a rakish angle.
- (of a vessel) having an appearance suggesting speed.
- dissolute; profligate
- dashing; jauntya hat set at a rakish angle
- nautical (of a ship or boat) having lines suggestive of speed
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].