This study evaluates the effects of particle and surface geometric features on the interface shear behavior of sand-geomaterial. Particle shape and size were adjusted for the sand, and surface roughness form and height were set for the geomaterial part. 3D printing technology was used to produce geomaterials in the desired form. A custom-made transparent interface shear box was developed to perform digital image processing. For macroscale response, peak and residual strengths and dilation angle were measured. Sliding percentage and shear band thickness were determined from digital image correlation analyses for the mesoscale response. The experimental results showed that the macroscale response parameters increased as the overall regularity of the sand particles decreased. The increase in mean particle size and roughness height led to an increase in macroscale parameters. Digital image correlation analyses showed that the sliding percentage had an inverse correlation with the shear band thickness in terms of the particle shape and the roughness height effects. The roughness form controlled the trend of mean particle size effects on the sliding percentage. Overall, the mesoscale parameters revealed the traces of interlocking response, particle kinematics, and the failure mechanism in the interface region. Thus, a bridge was established between meso- and macro-scale responses.