In recent years, designers have taken a quirky approach to baseball cap designs. For Spring 2022, Coach matched outerwear with baseball caps, while Courrèges worked them into a monochromatic ensemble. Still, the topper pairs well with just about anything, from tailored leather trousers to body-hugging minidresses, so there are plenty of ways to match it to your style. “When I think of the look that most inspires me, it's Celine's Spring 2021 runway, when the brand embraced the street style aesthetic of pairing a casual cap with basics like jeans and a leather jacket,” Madden says. Beyond that, Freeman argues, there is an allure to the baseball cap when one wears it with a certain amount of attitude. “Pulled down just above the brow line, baseball caps are a great way to cast a shadow over the eyes that will instantly add an appealing edge and mystique to an overall look.”