A neck supporting piece of apparel, such as a scarf, which includes an inflatable bladder in a neck portion and a tube coupled to the bladder and extending downward to a port easily accessible by the user while wearing the apparel in order to inflate and deflate the bladder, which serves as a neck cushion or pillow. While the neck portion may be configured to go behind the user's neck, the apparel also may include a connector to join the apparel together in front of the user, helping to keep the cushion formed around the user's neck. In addition, the scarf may include pockets at a position generally where the user's hands would lie when sitting or standing, such that tensioning the scarf with the user's arms may increase the cushioning effect of the pillow.