rak·ish 
/ˈreɪkɪʃ/ adjective
/ˈreɪkɪʃ/ adjective [more rakish; most rakish] 1 somewhat old-fashioned : having an unusual quality that is attractive and stylish
▪ a rakish smile ▪ He wore his hat at a rakish angle. [=tipped to one side in a way that is attractive] 2 old-fashioned, of a man : immoral and devoted to pleasure
▪ a rakish [=dissolute] aristocrat
▪ a rakish smile ▪ He wore his hat at a rakish angle. [=tipped to one side in a way that is attractive]
▪ a rakish [=dissolute] aristocrat
— rak·ish·ly adverb
▪ He smiled rakishly.
▪ He smiled rakishly.
