A headrest assembly includes upright supports that are partially disposed within a rear housing and interconnected to one another by a vertically adjustable guide bracket. A mounting plate is operably coupled to the guide bracket by a driveshaft of a first motor for driving horizontal movement of the mounting plate. A headrest bun is pivotally coupled to the mounting plate for rotating movement between upright and angled positions. A second motor is mounted to at least one of the upright supports and includes a vertical driveshaft coupled to the guide bracket for driving vertical movement of the guide bracket. The headrest bun includes first and second side bolsters that are pivotally coupled to a central support member between extended and retracted positions. The headrest assembly may further include an air moving device to provide ventilation or a heating feature to a user of the headrest assembly.