Dashingly disreputable (6)
(Other definitions for raffish that I've seen before include "Disreputable but attractive" , "Tawdry" , "Looking flashy and disreputable" , "Dashing" , "Attractively disreputable" .)
(Other definitions for rakish that I've seen before include "Disreputably dashing" , "Jaunty; dissolute" , "Jaunty and irresponsible" , "Jaunty; fast-looking (boat)" , "Dashing, devil-may-care" .)