raffishly

/ˈræfɪʃli/
adverb
  1. In a way that is slightly careless, unconventional, or disreputable but attractive.
    • He smiled raffishly and winked at his friend.
    • She dressed raffishly in a wrinkled linen jacket and boots.
    • The old sailor stood raffishly on the dock, pipe in hand.
Synonyms
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