/\  That is hardcore prep in action, he's saying that he's always at his leisure even when he's engaged in serious business and that other people's notions of sartorial correctness aren't governing him.

Penny loafers and ocbds with a tuxedo or Tretorns with a tweed 3/2 sack express the same insouciance, as do whimsical emblematic ties and motif trousers, but in order to pull it off you have to truly be insouciant, which often requires a lot of money and power.

Not supporting or denigrating these looks or attitudes, just making an anthropological observation. 

My favorite piece of crazy George H. W. Bush attire remains his tennis racquet emblematic tie, and I wish I had bought this tennis racquet printed ocbd O'Connell's had several years ago, as well as one with vintage cans of tennis balls on it.