rakish

adjectives

marked by up-to-dateness in dress and manners
"a dapper young man"; "a jaunty red hat"
dapper, dashing, jaunty, natty, raffish, rakish, snappy, spiffy, spruce
is derived from
rakishness
marked by a carefree unconventionality or disreputableness
"a cocktail party given by some...raffish bachelors"- Crary Moore
devil-may-care, raffish, rakish
is derived from
rakishness