From WordNet (r) 3.0 (2006):
rakish
adj 1: marked by up-to-dateness in dress and manners; "a dapper
young man"; "a jaunty red hat" [syn: dapper, dashing,
jaunty, natty, raffish, rakish, spiffy,
snappy, spruce]
2: marked by a carefree unconventionality or disreputableness;
"a cocktail party given by some...raffish bachelors"- Crary
Moore [syn: devil-may-care, raffish, rakish]