raffish

/ˈræfɪʃ/

Someone raffish is a bit of a scoundrel, carelessly making mischief. Your raffish classmate might constantly play mean practical jokes, always denying responsibility with a charming smile.

If you're raffish, you're a "rake" or a "cad." Though you're pretty much bad news, you pull off your dastardly deeds in an attractive manner. Someone with a raffish look is intriguing as well as disreputable. Raffish comes from riff-raff, "generally undesirable people," from the Medieval French rifle et rafle, "stealing from the bodies of the dead on the battlefield."

Definitions of raffish

1. adjective

   marked by a carefree unconventionality or disreputableness
   “"a cocktail party given by some...raffish bachelors"- Crary Moore”

   synonyms: devil-may-care, rakish

   unconventional

   not conventional or conformist
2. adjective

   marked by up-to-dateness in dress and manners
   synonyms: dapper, dashing, jaunty, natty, rakish, snappy, spiffy, spruce

   fashionable, stylish

   being or in accordance with current social fashions