Film: Catch Me If You Can
Year: 2002
Signature Look: Don Draper Plays Dress-Up

Catch Me If You Can's protagonist is a testament to the saying "fake it 'til you make it." Granted, you can probably "fake it" better than others if you're a young white male who looks like Leonardo DiCaprio, as seen in this film. We saw Frank Jr. go from emblem-blazered schoolboy to dapper airline pilot thanks to the help of a peak-lapeled navy blazer and tie bar. He also makes a case for short-sleeve button-down shirts, tortoiseshell eyeglasses, and white pants. That asymmetrical orange cardigan he pairs with tobacco brown loafers? Straight fire. Frank Jr., catch his style if you can.