Raffishness is the quality — the look, the air — of being raffish: a little not-respectable, still confident, still attractive. It is not one action, but the whole flavour of a person, a room, or even a street. You might talk about an old actor's raffishness, or the raffishness of a bar that feels charming and slightly naughty. Same slightly old-fashioned, slightly admiring tone as raffish. People who care a lot about being proper may not approve; the word itself usually sounds as if the speaker rather enjoys it.