1. Dashingly, carelessly, or sportingly unconventional or stylish; jaunty;
2. having a somewhat disreputable quality or appearance.

…Luke was the youngest of the three, handsome, in his twenties, a “researcher in technology and cyberculture and director of the Virtual Futures Conference,” according to his online CV. David Bausola looked like a rakish teacher, the sort of person who might speak at a conference on the literature of Aleister Crowley. He was a “creative technologist” and the CEO of the digital agency Philter Phactory.

From the post: Vocabulary Words from ‘So You’ve Been Publicly Shamed’
Source: So You’ve Been Publicly Shamed, by Jon Ronson (amazon.com)