Rakish

A tricorn trimmed with gold lace was set at a rakish angle over a wig of white curls that dropped down to his waist.

Source: tatoeba (897040)

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.

Source: wiktionary

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.

Source: wiktionary

[…]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.

Source: wiktionary