Merriam-Webster's Collegiate® Dictionary, 11th Edition
RAKISH
I. adjective
Etymology: 5rake
Date: 1706
of, relating to, or characteristic of a rake ; dissolute ,
II. adjective
Etymology: probably from 4rake; from the raking masts of pirate ships
Date: 1824
having a trim or streamlined appearance suggestive of speed , dashingly or carelessly unconventional ; jaunty