I. ˈrā-kish adjective
Etymology: rake (V)
Date: 1706
: of, relating to, or characteristic of a rake : dissolute
II. adjective
Etymology: probably from rake (IV); from the raking masts of pirate ships
Date: 1824
1. : having a trim or streamlined appearance suggestive of speed
a rakish ship
2. : dashingly or carelessly unconventional : jaunty
rakish clothes