The association between rider–saddle interaction and horse kinematics has been little studied. It was hypothesized that differences in a thigh block design would influence (a) rider–saddle interface pressures, (b) rider kinematics, and (c) equine limb/spinal kinematics. Eighteen elite sport horses/riders were trotted using correctly fitted dressage saddles with thigh blocks S (vertical face) and F (deformable face). Contact area, mean, and peak pressure between rider and saddle were determined using an on-saddle pressure mat. Spherical markers allowed for the measurement of horse/rider kinematics using two-dimensional video analysis. The kinematics of the equine thoracolumbosacral spine were obtained using skin-mounted inertial measuring units. Results were compared between thigh blocks (paired t-test p ≤ 0.05). With F, the contact area, mean, and peak pressure between rider and saddle were significantly higher (p = 0.0001), and the rider trunk anterior tilt was reduced, indicating altered rider–saddle interaction. The horse thoracic axial rotation and flexion/extension were reduced (p = 0.01–0.03), caudal thoracic and lumbar lateral bend was increased (p = 0.02–0.04), and carpal flexion increased (p = 0.01–0.05) with F compared to S. During straight-line locomotion when in sitting trot, thigh block F was associated with altered rider–saddle interaction and rider and equine kinematics, leading to a more consistent rider–saddle interface, a more upright rider trunk during stance, an increased horse thoracic stability and lumbar lateral bend, and forelimb flexion, supporting the importance of optimising rider–saddle–horse interaction.