Several classical dance complex movements, such as pointe, require body weight to be supported properly to avoid risk of foot injury. Regarding the choice of toe cap for pointe shoes, it is unclear which type can better alleviate pain symptoms and toe deviation angle in dancers. The aim of the current crossover study was to investigate the acute effect of using different types of toe caps among well-trained professional dancers on pain perception and toe deviation angle. Ten young female professional dancers volunteered to participate in the study. Each participant was tested during two separate sessions with an interval of 72 h in between. Participants were tested in the two sessions with a standard commercial or a customized prototype toe cap, always with pointe shoes, and in randomized order. An anteroposterior X-ray examination was performed separately for each participant and a visual analogue scale for pain perception was administered following each situation (with a standard commercial or a customized prototype toe cap). Significant amelioration was obtained when a customized toe cap prototype was used both for toe deviation angle and for visual analogue scale. Use of a customized toe cap prototype compared to a standard one may acutely reduce both toe deviation angle and pain in elite female professional dancers.