rakish
[adjective]
Synonyms: dashing, dapper, debonair, devil-may-care, jaunty, natty (informal), raffish, smart

[TahlilGaran] English Synonym Dictionary ▲

rak‧ish /ˈreɪkɪʃ/ 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: ⇒ rake¹(2)]

1. if a man looks rakish, or wears rakish clothes, he dresses nicely and looks confident and relaxed Synonym : 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

[TahlilGaran] Dictionary of Contemporary English ▲