WordWeb Online

1. Marked by up-to-dateness in dress and manners
   "a rakish young man";
   - dapper, dashing, jaunty, natty [informal], raffish, spiffy [N. Amer, informal], snappy [informal], spruce, pert
    
2. Marked by a carefree unconventionality or disreputableness
   "a cocktail party given by some...rakish bachelors";
   - devil-may-care, raffish

See also: fashionable, hip [informal], stylish, unconventional

Encyclopedia: Rakish