An apparatus for supporting the head of a person lying prone or on a side includes a base member that is configured to be worn on the head of the person and to rotate between a plurality of positions relative to a support surface upon which the base member rests. The base member defines at least one support member configured to contact the face of the person. A front support structure is mounted to the base member. The front support structure and the base member are cooperatively arranged to define a space between the front support structure and the face of the person wearing the apparatus. The at least one support member is configured to support the head of the person away from the front support structure when the person is lying prone or on a side and with the base member in any of the plurality of positions.