This application relates to inflatable apparel. In particular, this application discusses systems and methods for providing apparel that is both selectively inflatable and adapted for use as a pillow. The inflatable apparel may include any clothing or object that is adapted to be worn by a person and is selectively inflatable so as to act a cushion for the person wearing the apparel or of another. The inflatable apparel comprises an apparel item, such as a necktie, and an inflatable bladder. In some cases, the necktie is made to receive and retain the bladder in an inflated position or a deflated position. The bladder extends through at least a portion of the necktie. Additionally, when inflated, the bladder provides a pillow or cushion for use by the individual wearing the inflated necktie, or for use by an individual other than the person wearing the necktie.