Disclosed herein is an adjustable head supporting apparatus. In the illustrated examples, a garment encases the adjustable head supporting apparatus. The apparatus may include a contoured head element, a contoured shoulder element, and at least one connecting member connectable to each of the head element and the shoulder element. The at least one connecting member may be configured to link the head element and the shoulder element such that the at least one connecting member facilitates displacing the head element and the shoulder element to adjust spacing between them and the at least one connecting member. Displacement of a first end of the head element and displacement of a first end of the shoulder element can be independent of displacement of a second end of the head element and a second end of the shoulder element. The head element and the shoulder element may be encased within a fabric garment.