An article of headwear is disclosed that includes a support and a material element secured to the support. The support extends around a periphery of the headwear and has an elongate structure that defines a first end portion and a second end portion. The support is flexed such that the first end portion overlaps the second end portion to define a loop with an interior area, and the end portions may have mating undulating configurations. The material element is secured to the support and extends around the interior area of the loop to define an aperture for receiving a head of an individual. The support may be flexed to form multiple loops and place the headwear in a collapsed configuration.