New Era

Founded in 1920, New Era hats are synonymous with baseball, especially the fitted 59Fifty pro model, which has been the official on-field hat of the MLB since 1993. At some point they also became synonymous with hip hop and street culture, seen on the heads of just about every rapper since the '90s, including Tupac, Kendrick Lamar, Chance the Rapper and, of course, Jay Z.