The rapper/hop hop artist Pittbull usually performs in either a suit and tie or at the very least, a blazer.
I cringe a bit most of the times I see him, but I don't know why. Maybe it's because he resembles Dr. Evil a bit too much.
Sure, there are a few things that I can point to, such as the poorly shaped Windsor tie knots, the stuffy vests, the ugly dark-on-dark shirt/suit combinations, but at the end of the day, I can't quite put my finger on what exactly it is about the way he dresses that makes Pitbull look so awkward in his suits.
He looks like that mail-room guy forced to wear a tie, or the 21 year old guy at the hotel front desk that just hasn't grown comfortable wearing his cheap suit and tie, or the Woodbridge kid wearing a poorly fitting suit for the first time at his high-school Prom. I thought the same thing about Eminem when he wore a suit during the Encore tour (ca. 2004).
While I give the guy credit for trying to add a touch of class to his often shabbily dressed craft, most of the times he misfires.
I suspect that part of the problem lies with the fact that a suit and tie is not the most appropriate attire for a hip-hop performance. Sure, it can work well for other musical genres such as jazz or big band, but for hip hop, a suit and tie comes off as overly formal and/or stuffy. If a suit is to be worn at all, it ought to be somewhat more theatrical than the businesslike attire favoured by Pitbull.
Time for Pitbull to put his suits to sleep.