There has been little scientific investigation of the impact of dance shoes on foot motion or dance injuries. The pointed (plantar-flexed) foot is a fundamental component of both the technical requirements and the traditional aesthetic of ballet and jazz dancing. The aims of this study were to quantify the externally observed angle of plantar flexion in various jazz shoes compared with barefoot and to compare the sagittal plane bending stiffness of the various jazz shoes. Sixteen female recreational child dancers were recruited for 3D motion analysis of active plantar flexion. The jazz shoes tested were a split-sole jazz shoe, full-sole jazz shoe, and jazz sneaker. A shoe dynamometer measured the stiffness of the jazz shoes. The shoes had a significant effect on ankle plantar flexion. All jazz shoes significantly restricted the midfoot plantar flexion angle compared with the barefoot condition. The split-sole jazz shoe demonstrated the least restriction, whereas the full-sole jazz shoe the most midfoot restriction. A small restriction in metartarsophalangeal plantar flexion and a greater restriction at the midfoot joint were demonstrated when wearing stiff jazz shoes. These restrictions will decrease the aesthetic of the pointed foot, may encourage incorrect muscle activation, and have an impact on dance performance.