rakish

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

dapper jaunty natty raffish spiffy spruce dashing snappy devil-may-care

rakishly rakishness