Adjectives

(s)dapper, dashing, jaunty, natty, raffish, rakish, spiffy, snappy, sprucemarked by up-to-dateness in dress and manners“a dapper young man”, “a jaunty red hat”
(s)devil-may-care, raffish, rakishmarked by a carefree unconventionality or disreputableness“a cocktail party given by some … raffish bachelors” (Crary Moore)