Plantar heel pain is one of the most common musculoskeletal conditions affecting the foot and it is commonly experienced by older adults. Contoured foot orthoses and some heel inserts have been found to be effective for plantar heel pain, however the mechanism by which they achieve their effects is largely unknown. The aim of this study was to investigate the effects of foot orthoses and heel inserts on plantar pressures in older adults with plantar heel pain. Thirty-six adults aged over 65 years with plantar heel pain participated in the study. Using the in-shoe Pedar(®) system, plantar pressure data were recorded while participants walked along an 8 m walkway wearing a standardised shoe and 4 different shoe inserts. The shoe inserts consisted of a silicon heel cup, a soft foam heel pad, a heel lift and a prefabricated foot orthosis. Data were collected for the heel, midfoot and forefoot. Statistically significant attenuation of heel peak plantar pressure was provided by 3 of the 4 shoe inserts. The greatest reduction was achieved by the prefabricated foot orthosis, which provided a fivefold reduction compared to the next most effective insert. The contoured nature of the prefabricated foot orthosis allowed for an increase in midfoot contact area, resulting in a greater redistribution of force. The prefabricated foot orthosis was also the only shoe insert that did not increase forefoot pressure. The findings from this study indicate that of the shoe inserts tested, the contoured prefabricated foot orthosis is the most effective at reducing pressure under the heel in older people with heel pain.