Definition of "raffish"

Billie Eilish wants you to know she is in charge, brash and self-assured enough to scrap the raffish image that helped garner her a world of fans in favor of something a little more … adult.

2021 May 4, Ruth La Ferla, “On That Bombshell Billie Eilish Cover for British Vogue”, in The New York Times‎

The smokers' most raffish outsider, Comstock, appeared to do nothing but smoke; Chris had never seen him inside the building.

2022, Jennifer Egan, “i, the Protagonist”, in The Candy House

I had met the man before this in the village, and detested him on sight; there was something indescribably raffish in his looks and ways that raised my gorge; […]

1891 February–December, Robert Louis Stevenson, chapter XV, in In the South Seas […], New York, N.Y.: Charles Scribner’s Sons, published 1896

He bowed cordially to the lady in charge of Miss de Barral’s education, whom he saw in the hall engaged in conversation with a very good-looking but somewhat raffish young gentleman.

1914, Joseph Conrad, “The Governess”, in Chance‎, London: Methuen

He wore a neat dark overcoat, brown shoes, and a bowler hat rather on one side; his appearance was, in fact, genteel, though his air was a trifle raffish.

1919, Anthony Hope, chapter VII, in The Secret of the Tower‎

Altogether the city [Las Vegas] is one of the most amiably raffish communities in the nation—an assembly of glittering chrome and flaming colors by day, a flowering jungle of glowing neon and flashing lights by night.

1951 February 11, Gladwin Hill, “Atomic Boom Town In the Desert”, in The New York Times‎