1. marked by up-to-dateness in dress and manners

Similar word(s): fashionable, stylish, dapper, dashing, jaunty, natty, snappy, spiffy, spruce

2. marked by a carefree unconventionality or disreputableness

Similar word(s): unconventional, raffish

Sentences with rakish as an adjective:

- ... the rakish Dennis Quaid, a Houston native who is moving to Texas in a couple of years and wants it to become "the new Hollywood." (Houston Chronicle, 6/8/2007)