Florsheim Kearny in Gray Suede, $65
Hamilton 1883 Baja Pullover, $225
Unis Gio in Red Clay, $228

Gray doesn’t necessarily have to mean gloomy. Go preppy without looking like Zach Morris in a slim pair of red chinos—cuffed of course. Add a pop-over shirt in an on-point baja print and you’ve got that casual summer style on lock.