raffish

Adjective
  1. Marked by up-to-dateness in dress and manners (synset 300975112)
    "a dapper young man"; "a jaunty red hat"
    similar to: fashionable, stylish - being or in accordance with current social fashions
    same as: dapper, dashing, jaunty, natty, rakish, snappy, spiffy, spruce
  2. Marked by a carefree unconventionality or disreputableness (synset 300611718)
    "a cocktail party given by some...raffish bachelors"
    similar to: unconventional - not conventional or conformist
    same as: devil-may-care, rakish

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