WordNet sense 1 (marked by up-to-dateness in dress and manners):

dapper, dashing, jaunty, natty, raffish, snappy, spiffy, spruce

WordNet sense 2 (being or in accordance with current social fashions):

fashionable, stylish

WordNet sense 3 (marked by a carefree unconventionality or disreputableness):

devil-may-care

WordNet sense 4 (not conventional or conformist):

unconventional