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Adjective: rakish  rey-kish
  1. Marked by up-to-dateness in dress and manners
    "a rakish young man";
    - dapper, dashing, jaunty, natty, raffish, spiffy, snappy, 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, happening, stylish, unconventional

Encyclopedia: Rakish