To reveal the influence of rubber particles on the mechanical properties of calcareous sand under the large-displacement shear effects of earthquakes and waves, indoor ring shear tests were conducted on rubber particle-calcium sand mixtures. The effects of rubber particle size and content on the mechanical properties of calcareous sand were studied via indoor ring shear test. Then, based on PFC3D, a numerical model of a ring shear test that can restore the shape of calcareous sand particles is established, and a mesomechanical analysis of mixed sand is carried out. The results showed that the effect of the rubber particle content on the crushing characteristics and strength of calcareous sand was significant and that the effect of the particle size was small. The rubber content causes a gradual decrease in the peak strength and particle crushing rate and increases the deformation stability of the mixed sand. The softening coefficient and relative crushing rate were significantly reduced to 0.01–0.06 and 0.28–1.2%, respectively, at 40% rubber content. The numerical simulations and experimental results were in good agreement. An increase in the rubber content significantly influences chain development, which explains the macroscopic mechanical properties of mixed sand at the fine level.