Definition of "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.

1889, Jerome K. Jerome, chapter 18, in Three Men in a Boat […] ‎

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.

1904 March 26, A[rthur] Conan Doyle, “The Adventure of Charles Augustus Milverton”, in The Return of Sherlock Holmes, New York, N.Y.: McClure, Phillips & Co., published February 1905

[…] 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.

1908 June, L[ucy] M[aud] Montgomery, Anne of Green Gables, Boston, Mass.: L[ouis] C[oues] Page & Company, published August 1909 (11th printing)

[…] 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."

2007 June 8, Houston Chronicle

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

2009 August 4, Dan Martin, “Jarvis Cocker writes songs for Russell Brand”, in The Guardian‎

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.

2020 August 28, Thomas Vinciguerra, “Comfort Viewing: 3 Reasons I Love ‘The Sting’”, in The New York Times‎

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.

1848 November – 1850 December, William Makepeace Thackeray, chapter 5, in The History of Pendennis. […], volumes (please specify |volume=I or II), London: Bradbury and Evans, […], published 1849–1850

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 March – 1853 September, Charles Dickens, chapter 14, in Bleak House, London: Bradbury and Evans, […], published 1853

The arduous task of converting a rakish lover.

1856 February, [Thomas Babington] Macaulay, “Oliver Goldsmith”, in T[homas] F[lower] E[llis], editor, The Miscellaneous Writings and Speeches of Lord Macaulay, new edition, London: Longman, Green, Reader, & Dyer, published 1871