Longman Dictionary of Contemporary English homepage

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: RAKE12

rakish

 adjective
     
rak‧ish
1 if a man looks rakish, or wears rakish clothes, he dresses nicely and looks confident and relaxed [= stylish]:
a rakish uniform
2

at a rakish angle

DC 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
Definition from the Longman Dictionary of Contemporary English
Advanced Learner's Dictionary.

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