Although high heels are known to affect the biomechanics of human movement, most notably by increasing forefoot plantar pressure, it is commonly worn due to the influence of fashion. To deal with the resulting clinical issues, some prescriptions include the use of cushioning pads to redistribute the plantar loads and increase comfort. This preliminary study has sought to investigate whether auxetic foam would be a good candidate for the redistribution of plantar loafing in the forefoot when compared to a more traditional material. From the results obtained, it was shown that auxetic foam demonstrated a decrease in forefoot peak plantar pressure while a commercial product, a material traditionally used for plantar cover paddings, increased pressure in the region of the second–fourth Metatarsophalangeal Joint. This demonstrates the potential for auxetic materials to become the material of choice for such applications, especially since it can be further remodeled until its properties can produce a significant forefoot pressure reduction.