• Etymology Today from M-W: raffish \RAF-ish\

1 : marked by or suggestive of flashy vulgarity or crudeness
2 : marked by a careless unconventionality : rakish

"Raffish" sounds like it should mean "resembling the raff." But what is "raff"? Originally, "raff" was rubbish. That term derives from the Middle English "raf," and it was being used for trash and refuse back in the 1400s. At around the same time, English speakers were also using the word "riffraff" to mean "disreputable characters" or "rabble." The origins of "riffraff" are distinct from the "rubbish" sense of "raff"; "riffraff" derives from an Anglo-French phrase meaning "one and all." By the mid-1600s, the similarities between "raff" and "riffraff" had prompted people to start using the two words as synonyms, and "raff" gained a "rabble" sense. It was that ragtag "raff" that gave rise to the adjective "raffish" in the late 1700s.

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