I. ˈrākish, -kēsh adjective
Etymology: rake (VII) + -ish
: of or relating to a rake : licentious , wanton
he combined the studies and the rakish life — P.E.More
II. adjective
Etymology: probably from rake (V) + -ish; from the raking masts of pirate ships
1. : having a smart stylish appearance suggestive of speed
a rakish ship
in his battered, rakish roadster — MacKinlay Kantor
2. : negligent of convention or strict formality : careless , jaunty , sporty
the languid rakish habit of wearing a hat indoors at his desk — American Guide Series: North Carolina