Pendleton Board Plaid Lined Wool Button-Up Shirt For that Beach Boys-inspired vintage aesthetic, you’ll want to throw on Pendleton’s iconic Board flannel button-down.

The problem with a check dress shirt is that it can look a little college bro if not styled properly. Wear one in preppy, athletic hues like cobalt, orange, or red, and with a big, fat tie, and ...

The Borrowed-from-the-Boys: Frame Baja plaid shirt, $268 The Rodeo Ready: J.Crew Western shirt , $118 Dressing for the transitional season can be notoriously tough to navigate.