Era: Spring 2011
As seen on: Panamanian drug lords; extra-privileged teenagers; Emeraldo Zegna models 

Prior to the 2011 Kentucky Derby, Brady walks into Tom Ford on Madison Avenue and asks to be styled like a white-collar fugitive living under-the-radar on a yacht boat in Saint-Tropez. This is the look of an unscrupulous financier trying to sneak through customs at Paris' Charles de Gaulle Airport. Behold the smirk of a man who has at least a dozen Picasso originals hidden in an explosives resistant safe.