Raffish people and places are not very respectable but are attractive and stylish in spite of this. He was handsome in a raffish kind of way. behaving or dressing in way which is not respected by many people but which is still confident and attractive (riffraff)
marked by a carefree unconventionality or disreputableness; "a cocktail party given by some raffish bachelors"- Crary Moore
marked by smartness in dress and manners; "a dapper young man"; "a jaunty red hat"