A fitting system for a hat includes a band configured to be coupled to the hat; and a resilient member disposed within at least a portion of the band. The resilient member includes a first end, a second end, and an intermediate portion between the first and second ends. A crown extension and a crown extension bottom edge extend downwardly below a circumferential bottom edge of the hat wherein the resilient member is only positioned within a front band portion, a first side band portion, a second side band portion, and the crown extension. The first side band portion and the second side band portion are adapted to attach to the crown to form side gaps. Each of the side gaps are designed to receive the top portion of the user's ear so that the hat is designed to sit lower on the user's head without impinging upon the user's ears while the hat is being worn. A system and method are provided.