The Gents Director's Cap is best described by what it isn't. "It's not the oversized, flat-brimmed hat with the sticker on top," says Gents founder Josh Reed, a Calvin Klein vet who took up work at a talent agency in Los Angeles, the city where everyone wears lids all the time. But while great denim and T-shirt lines were plentiful in Hollywood, Reed says, "I noticed it was really hard to find a sleek, more upscale cap. So I started developing them as a hobby." Reed launched his e-commerce platform late last year, and has since added beanies, baseball raglans, and tees (he keeps things simple there; look elsewhere if you want anything beyond black, white, or gray).
The Director's Cap – spotted on Hollywood types like Pattinson and DiCaprio – remains his baseline and best seller. And with good reason: It's customizable by size, color, logo, and monogram. We're sticking with the clean and sophisticated black, which wears well from the office to the gym and back again. While its velvety brushed cotton blend appears underwhelming from afar, it's remarkably well-fitting, with a flexible band, a curved, well-proportioned brim, and – Reed reiterates this point – "no air gap," meaning it sits right where it should, midway down your brow, with just enough room leftover for a pair of retro-cool sunglasses. [$49; gentsco.com]