Roundness/angularity is a vital shape descriptor that significantly impacts the mechanical response of granular materials and is closely associated with many geotechnical problems, such as liquefaction, slope stability, and bearing capacity. In this study, a series of biaxial shearing tests are conducted on dual-size aluminum circular and hexagonal rod material. A novel image analysis technique is used to estimate particle kinematics. A discrete element model (DEM) of the biaxial shearing test is then developed and validated by comparing it with the complete experimental data set. To systematically investigate the effect of roundness/angularity on granular behavior, the DEM model is then used to simulate eight non-elongated convex polygonal-shaped particles. Macroscopically, it is observed that angular assemblies exhibit higher shear strengths and volumetric deformations, i.e., dilations. Moreover, a unique relationship is observed between the critical state stress ratio and particle roundness. Microscopically, the roundness shows a considerable effect on rotational behavior such that the absolute mean cumulative rotation at the same strain level increases with roundness. A decrease in roundness results in relatively stronger interlocking, restricting an individual particle’s free rotation. Furthermore, the particles inside the shear band exhibit significantly higher rotations and are always associated with low coordination numbers. Generally, the geometrical shape of a particle is found to have a dominant effect on rotational behavior than coordination number.