Also popular: The bolero hat, otherwise known as the “Annie Hall” hat, made popular by Diane Keaton’s character in the classic Woody Allen film. “This hat is obviously ’70s-inspired, but in a very preppy way,” says Roberts. Think about wearing it with button-down shirts or blouses, khaki shorts, and other prep school styles. And it’s also important that you get the look just right. “The hat should sit on the back of your head and show the front of your hairline,” says Roberts.

And while you could keep you hair sleek and straight for this style, why not opt for something a little different? Dizon is a fan of braids. “Besides leaving the hair down — wavy or straight — you can mix it up with the tried and true three-strand braid, or even four-strand braid.”