Ailing

raffish \RAF-ish\, adjective:

1. Characterized by or suggestive of flashy vulgarity, crudeness, or rowdiness; tawdry.
2. Marked by a carefree unconventionality or disreputableness; rakish.

The speaker was in his forties, an attractive-looking man with a black eye patch that gave him the raffish look of an amiable pirate.
-- Sidney Sheldon, The Best Laid Plans

Sometimes we would go to the Gargoyle Club, . . . but it was too full of raffish upper-class drunks for my taste.
-- John Richardson, The Sorcerer's Apprentice

We are told about Bacon's taste for raffish, lower-class lovers, his penchant for gambling and his almost complete disregard for money.
-- Michiko Kakutani, "Portrait of a Portraitist Of a Century's Horrors", New York Times, December 14, 1993

Raffish derives from the noun raff (chiefly used in the compound or duplicate, riffraff), meaning "people of a low reputation."