a. Resembling, or having the character of, raff, or a raff; worthless; low. [ 1913 Webster ]

A sad, raffish, disreputable character. Thackeray. [ 1913 Webster ]

2. Mildly disreputable; disregarding conventional morality; charmingly dissolute{ 3 } or nonconformist. [ PJC ]

Tales of his [ Ted Kennedy's ] drinking and raffish behavior have become part of his public persona, often lumped under a vaster damnation known as “the character issue”.
. . .
He appears to compartmentalize his off-duty conduct and his Senate responsibilities; during dozens of interviews for this article, with friends and foes, not one could cite an instance in which drinking appeared to impair him professionally. His adversaries grumble about it anyway; friends portray it as relatively harmless and charming.

Orrin Hatch, the conservative Utah Republican who is also a Mormon, tells this story with what he describes as “a tremendous brotherly affection.” Two days before the Senate adjourned in October 1988, Hatch took a call from Frank Madsen, a former aide who had moved to Boston to supervise 200 young Mormon missionaries. Would Hatch come speak to them? Would he bring Kennedy? Would he ask Kennedy to reserve Faneuil Hall for the event?

With some misgivings, Hatch agreed to try. Shortly before midnight, he found Kennedy and Chris Dodd in the Capitol. Neither was feeling any pain.

“Ted, I've got a favor to ask.”

Kennedy wrapped an arm around Hatch. “Done!”

Hatch held up a restraining hand. “No, hear me out. You remember my aide, Frank Madsen -- ”

“Great fellow! Great fellow!”

“He's now in Boston -- ”

“My home town! My home town!”

Hatch eventually made his request. Kennedy assented. Hatch returned to his office, typed out the agreement and sent it to Kennedy's office. The next day, Hatch spied Kennedy reading the memo. “Orrin, ” Kennedy called in mock horror, “what else did I agree to?” Three months later, in January 1989, Hatch and Kennedy stood elbow-to-elbow in Faneuil Hall, addressing the Mormon missionaries. Rick Atkinson, Washington Post, Sept. 29, 1990 [ PJC ]

3. Dissolute; rakish. [ PJC ]

Of all such places, Santa Fe may well be the least raffish. At least in the off-season, it's a town that goes to bed early, showing all the prudent reserve of a city of bankers and claims adjusters. In the historic center, a visitor searches in vain for tawdry traces of the hard-drinking, wild-womanizing, heavy-gambling cowboy town this once must have been. Brad Leithauser (“Santa Fe”, in New York Times Magazine / May 13, 2001). [ PJC ]

Over the years, it [ Macau ] has maintained a downright raffish atmosphere, complete with warring gangsters. Yvette Ziols. [ PJC ]

4. Vulgarly gaudy; cheap and tawdry; as, a tendency toward gaudy jewelry, bright colors and generally raffish dress. [ PJC ]

A lonely orphan, Lilli, lands a job with a raffish and run-down carnival. The wide-eyed and innocent orphan is mesmerized by its gritty, tawdry glamour. Anonymous review of the play Carnival (https://web.archive.org/web/20040904064952/http://www.kt-online.org/plays/02-carnival-frame.html) [ PJC ]

4. Appealing to or frequented by dissolute or disreputable people; as, a raffish night club. [ PJC ]