rak ‧ ish /ˈreɪkɪʃ/ BrE AmE adjective
[ Sense 1-2: Date: 1800-1900 ; Origin: Probably from rake 'to slope backward' (17-21 centuries) ; because of the sloping masts of pirate ships. ]
[ Sense 3: Date: 1700-1800 ; Origin: ⇨ ↑ rake 1 (2) ]
1 . if a man looks rakish, or wears rakish clothes, he dresses nicely and looks confident and relaxed SYN stylish :
a rakish uniform
2 . at a rakish angle if you wear a hat at a rakish angle, you do not wear it straight, and this makes you look relaxed and confident
3 . old-fashioned a rakish man has a lot of sexual relationships, wastes money, and drinks too much alcohol
—rakishly adverb