rakish

rakish \REY-kish\, adjective:

1. Smart; jaunty; dashing.
2. Of a vessel: having an appearance suggesting speed.
3. Like a rake; dissolute: rakish behavior.

Just as they stepped into the house Beard remembered that it was Patrice's afternoon off, and there she was, at the head of the stairs, in rakish blue eye patch, tight jeans, pale green cashmere sweater, Turkish slippers, coining down to meet them with a pleasant smile and the offer of coffee as her husband had made the introductions.
-- Ian McEwan, Solar
General Bernard Rutkowski, his cap set at a slightly rakish, angle strode along the tunnel.
-- Fletcher Knebel, Charles Waldo Bailey, Seven days in May
Rakish enters the English lexicon in the 1700s, but rake, as in "immoral person," goes back further, possibly descended from the Middle English rakel, "headstrong."