Improved shoe inserts (22, 56, 63) are provided which are designed for placement within the toe regions (37, 52, 64) of shoes (34, 50, 62) to provide enhanced comfort to the shoe wearers. The inserts (22, 56, 63) are preferably cut from initial pillow-shaped bodies (20) to give the custom-designed inserts (22, 56, 63). The inserts (22, 56, 63) are designed to substantially occupy the distal end of the shoe toe region and present a proximal toe-engaging face that substantially spans the cross-sectional dimension of the toe-region. The inserts (22, 56, 63) are preferably formed of heat-sensitive, viscoelastic, polyurethane foam material.