When in doubt, go for stripes, plaid, and a bow tie.
Nate (background): Shirt, $45, Polo from James Davis; pants, $75, Kuhl from James Davis; sweater, $88, French Connection from Lansky 126.
On Ryan: Shirt, $108, Lansky 126; bow tie, $40, from Reginald Beam; sunglasses, $20, Lansky 126.