rakish

adj

1. Dashingly, carelessly, or sportingly unconventional or stylish; jaunty; characterized by a devil-may-care unconventionality; having a somewhat disreputable quality or appearance.

   “I did not catch what was going on at first, and was, therefore, extremely surprised at noticing George hurriedly smooth out his trousers, ruffle up his hair, and stick his cap on in a rakish manner at the back of his head, and then, assuming an expression of mingled affability and sadness, sit down in a graceful attitude, and try to hide his feet.”

   “A little later a rakish young workman, with a goatee beard and a swagger, lit his clay pipe at the lamp before descending into the street.”

   “[…]Anne, who had dropped into her seat, gasping for breath, with a forgotten lily wreath hanging askew over one ear and giving her a particularly rakish and disheveled appearance.”

   “[…] 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."”

   “Jarvis Cocker and Russell Brand have both found fame as rakish British iconoclasts.”

2. (dated)Like a rake; dissolute; profligate.

   “Poverty seems as if it were disposed, before it takes possession of a man entirely, to attack his extremities first: the coverings of his head, feet, and hands are its first prey. All these parts of the Captain’s person were particularly rakish and shabby.”

   “The door was open, and the hall was blocked up by a grand piano, a harp, and several other musical instruments in cases, all in progress of removal, and all looking rakish in the daylight.”

   “The arduous task of converting a rakish lover.”