In this case—caught at a Teach for America benefit with J.Crew’s Mickey Drexler at his side—he’s sporting a pitch-perfect example of the style that got him where he is. It’s not all perfect or on-trend. A lesser blogger might complain about the utility parka or jeans that could be characterized as paternal in nature, but we’re more interested in the big picture. In this case, that means an unforced approach to style that’s not afraid to wear something colorful and functional. And a having a pitch-perfect madras shirt in your closet certainly doesn’t hurt.