We analysed the static footprints of 1846 skeletally mature individuals to establish the influence of the age at which shoe-wearing began on the prevalence of flat foot. The incidence was 3.24% among those who started to wear shoes before the age of six years, 3.27% in those who began between the ages of 6 and 15 and 1.75% in those who first wore shoes at the age of 16 (p < 0.001). Flat foot was highest in those who, as children, wore footwear for over eight hours each day. Obese individuals and those with ligament laxity had a higher prevalence of flat foot (p < 0.01 and p < 0.0001, respectively). Even after adjusting for these two variables, significantly higher rates of prevalence were noted among those who began to wear shoes before the age of six years. Our findings suggest an association between the wearing of shoes in early childhood and flat foot.