rakish in WordNet English dictionary

1. marked by up-to-dateness in dress and manners
   "a dapper young man"; "a jaunty red hat"
   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
   devil-may-care  raffish  rakish