A headrest assembly includes a centrally disposed headrest bun having an upper portion and an adjustable lower portion. The adjustable lower portion is configured to move between extended and retracted positions relative to the upper portion. First and second side supports are operably coupled to the headrest bun on opposite sides of the headrest bun. The first and second side supports are operable between upright and deployed positions relative to the headrest bun. The adjustable components of the headrest assembly make for a headrest assembly that is operable between neutral and surround configurations.