Menswear-inspired hats like fedoras and newsboy caps have been making a comeback, but the question is: how do you wear a newsboy cap without looking like a character in a Dickens novel? It’s all about finding a chic, updated hairstyle to go with your cute cap. “A lot of women think when you wear a hat you don’t have to fix your hair,” says Sanders. “But you want to call attention to your hairstyle — whether it’s beachy waves or a sleek side pony. That way the hat is a stylish accessory as opposed to a problem-solver.”