2. The Gingham Shirt — Go, go gingham! This staple is totally sharp — especially against a nice tan. But, really, when you want some country club swag, these guys go all the way. New England not your thing? Switch it up with a jean jacket or a contrast patterned tie.

Frank & Oak Hawkes Shirt In Sapphire, $45, available at Frank & Oak; Ledbury The Navy Parker Gingham Spread Slim Fit, $135, available at Ledbury.