There are eighteen alternative spellings for riffraff in the OED including rifraf and riff-raff. The word dates back to the early 14th century when the phrase rif and raf meant everything, down to the last little bit. By the end of the same century, it became descriptive of common people in the derogatory sense of the word that we know today. Rif and raff also has etymological connections to rifle, as in to plunder. The plundering and sacking of towns and cities was a common occurrence in The Middle Ages and those who took part were generally despised as riffraff. By the 16th century, the term riffraff had become synonymous with the scum and dregs of society. Its offshoot raffish, although deriving from the same etymology, is far less derogatory in that raffish means charmingly or stylishly roguish. See also Raft.