A headgear-earwear assembly and a method of assembling the same. The headgear-earwear assembly can include an earwear and a headgear adapted to be coupled together. The earwear can include an elongated member, such as a cord, and an earpiece coupled to the elongated member. The headgear can include a major surface and a channel oriented substantially along the major surface of the headgear. The channel can be configured to removably house at least a portion of the length of the elongated member. The headgear can further include an aperture positioned adjacent the channel and open to the channel. The aperture can include an undulating shape along at least a portion of its length. The method can include positioning at least a portion of the elongated member in the channel, such that at least a portion of the length of the elongated member is removably housed in the channel.