The analysis of sands, and the foundation systems with which they interact, are largely dependent on macroscale behavioral parameters that represent the aggregated response of several microscale characteristics. This research paper examines the influence of surface texture, or smoothness, on the behavior of sands. The challenge of estimating or measuring smoothness, due to its microscale feature domain, is addressed through an examination of six artificially graded sand specimens. These specimens are evaluated both visually and numerically to characterize their surface smoothness. The first approach described is a simple visual method that uses a smoothness scale consistent with those of roundness and sphericity. This method, which can be performed with a tool as simple as a hand lens, evaluates a group of representative particles collectively. The second approach is also a visual evaluation, but it utilizes images obtained via scanning electronic microscopy, traditional optical microscopy, and newer low-cost digital microscopes that can be rapidly connected to a smartphone or laptop. To validate these visual estimates, a novel third approach is introduced. This approach is a more objective numerical analysis measurement technique that enables rapid and economic quantification of smoothness. This technique may assist both practitioners and academics in their understanding of the macroscale response of coarse-grained soils. In addition to the visual methods, this research also conducted several laboratory index tests to observe the mechanical behavior of the specimens, considering their particle shape and surface smoothness properties. The results indicate that angular sands have greater minimum and maximum void ratios, a larger difference between the minimum and maximum void ratios, greater critical state friction angles, and greater flow rates through an orifice of fixed size. When adjusted for surface smoothness using the proposed approach, the behavior of the sands—particularly the limit void ratio results—appears to be more predictable in some cases. These results provide additional evidence of particle smoothness contributing to the strength behavior of sand, which may be particularly useful in the domains of slope stability, land reclamation, soil–structure interaction, and soil dynamics.