Idiopathic toe walking (ITW) is a gait deviation characterized by forefoot contact with the ground, sometimes observed in children, that alters ankle kinematics, possibly leading to health-related issues. When studying foot and ankle gait deviations, the adoption of a single-segment foot model entails a significant simplification of foot and ankle movement, and thus may potentially mask some important foot dynamics. Differences in ankle kinematics between single- (conventional gait model, PiG, or Davis) and multi-segment (Oxford foot model, OFM) foot models were investigated in children with ITW. Fourteen participants were enrolled in the study and underwent instrumented gait analysis. Children were asked to walk barefoot and while wearing a foot orthosis that modified the ankle movement pattern toward a more physiological one without blocking foot intrinsic motion. ITW gait abnormalities, e.g., the absence of heel rocker and the presence of anticipated forefoot rocker, were found/not found according to the foot model. Walking conditions significantly interacted with the foot model effect. Finally, the different characterization of gait abnormalities led to a different classification of ITW, with a possible impact on the clinical evaluation. Due to its closer adhesion to ankle anatomy and to its sensitivity to ITW peculiarities, OFM may be preferable for instrumented gait analysis in this population.