Rakish

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.

Harold Gould as Kid Twist (with a great mustache) wore the best Homburg in recent memory, and Redford always kept his fedora atilt at just the right, rakish angle.

If rakish dukes were one's thing.

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.