Raffish: Disreputable, vulgar, sleazy; also (and more commonly now) mischievous, offbeat, showing an attractive disregard for conventional behavior.
I’ve been doing some research into brand names that end in -ish, so a recent tweet from word guy James Harbeck caught my attention:
The adjectival suffix -ish signifies “having the qualities of [the noun it’s attached to].” So if raffish is “having the qualities of raff,” what is “raff”?
It turns out that raff goes back to Middle English. Back in the late 14th century, according to the OED, it meant “a class or group of people (perh. with negative connotations.” By the mid-1400s it also meant “worthless material” or rubbish, a meaning that persisted through the early 20th century. We still use riff-raff to mean “disreputable people”; that usage has cognates in many European languages—French rif et raf, Italian de riffa e de raffa, Danish ripsraps—where it means something closer to “every single one.” Oxford Dictionaries Online claims that raffish was shortened from riffraff + ish, but other dictionaries don’t concur.
The Online Etymology Dictionary credits Jane Austen with the first published usage of the “disreputable” sense of raffish, in 1801, but gives no citation; the OED doesn’t mention Austen and antedates the usage to 1795, in a book called Elisa Powell. (“They returned to the parlour, laughing, and saying one to the other, ‘Did you ever see any thing so raffish! He will certainly become a mere student.’”) The “attractive disregard” sense goes back only to 1906, and didn’t really pick up steam until the middle of the 20th century, according to Ngrams for American and British English. Maybe the dashing flyboys of the RAF (Royal Air Force) nudged the word into positive territory, or perhaps it was influenced by rakish (now “jaunty, dashing,” but originally “disreputable”—as in like a rakehell).
Tennessee Williams used raffish to vivid effect in his stage directions for the opening of A Streetcar Named Desire (1947):
The exterior of a two-story corner building on a street in New Orleans which is named Elysian Fields and runs between the L & N tracks and the river. The section is poor but, unlike corresponding sections in other American cities, it has a raffish charm.
To learn how the -ish suffix became an independent word (“Hungry?” “Yeah, ish”), read Gretchen McCulloch’s essay for Lexicon Valley.