School Daze

Take a page out of the prep school dress code by wearing a crested blazer, but pair it with a micro-print shirt and a blinged out watch to eschew any perceived stuffiness. Wool blazer ($2,925) by Gucci; cotton shirt ($525) by Lemaire, at Nordstrom; Oyster Perpetual Datejust ($14,550) by Rolex.

Shot on location at The Greater Good Hair by Vincent Sullivan using British Barbers Association Makeup by Julie Wiktowy using Best Look Forward Cosmetics