Rakish \REY-kish\ , adjective;
1. Smart; jaunty; dashing
2. Of a vessel: having an appearance suggesting speed
3. Like a rake; dissolute: rakish behavior
Rakish dates to 1706 and is a combination of rake + -ish. There are a couple of etymologies for rake, one is the "toothed tool" which comes from Old English raca ("rake") and earlier ræce which derives from Proto-Germanic *rak- ("gather, heap up"). This is not the one that applies to rakish. That rake is a 1650's shortened form of rakehell which dates to the 1540's and means "debauchee". Rakehell is probably an alteration of Middle English rakel ("hasty, rash, headstrong") which is related to raken ("to go, proceed"). Both Middle English forms derive from Old English racian, and that's as far as it has be traced. The OED doesn't have the same etymology as I just gave for rakehell, so you should take it with a grain of salt I suppose.
Today's word and the first definition were both taken from Dictionary.com's 'Word of the Day' for Friday, January 28
Etymologies come from the Oxford English Dictionary and/or Etymonline.com