A reversible headwear (100), such as a beanie, includes a reversible headwear body (110) and a pom-pom (150) connected thereto. The reversible headwear body (110) is adjustable between a first configuration and a second configuration. The headwear body (110) has a first surface (112) and an opposite second surface (114). The first and second surfaces (112, 114) correspond to outer and inner surfaces respectively in the first configuration of the headwear body (110), and to the inner and outer surfaces respectively in the second configuration of the headwear body (110). The headwear body (110) has a through-hole (130) extending from the first surface (112) to the second surface (114). The pom-pom (150) is configured to be connected to the headwear body (110) to allow movement of the connected pom-pom (150) through the through-hole (130) for positioning the connected pom-pom (150) over the opening on or over the outer surface when the headwear body (110) is in the first configuration or the second configuration.