The hat is arguably the most challenging accessory in the fashion game. At the time of procurement, it feels like an essential. Post purchase, it’s often the cause of frustration when trying to style it without conveying a trying-too-hard vibe. The reality? A great hat can take an otherwise basic outfit to the next level, instantly adding polish and It-girl factor. For fall, luxurious materials—wool, leather, shearling—make a look stand out, whether it’s a baseball cap balancing off-duty casual or a fedora topping off polished separates. Ahead, our must-haves for fall and how we’ll be styling them.