rakish

Resembling or given to the practices of a rake; given to a dissolute life; lewd; debauched.

Jaunty.

Nautical, having an unusual amount of rake or inclination of the masts, as a vessel. The piratical craft of former times were distinguished for their rakish build.

Dissolute; lewd; debauched.

Having a saucy appearance indicative of speed and dash.

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

like a rake; dissolute; profligate

marked by a carefree unconventionality or disreputableness

marked by up-to-dateness in dress and manners