Buy It Now: The Knottery, $30
What Douchebags Wear: Broken-in caps with a curved brim

Wool baseball caps can make your head hot. Opt for a cotton five-panel like this patterned hat from The Knottery. Available in a bunch of lightweight fabrics and dope prints from camo to dots, you'll be able to feel the breeze on your head while keeping your cool in more ways than one.