rakish

adjective2

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

   • a hat worn at a rakish angle
2. •
   (old-fashioned) Like a rake; dissolute; profligate.

   • 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. — 1852