Natural soil deposits can consist of particles with a wide range of sizes. In current practice, the assessment of shear strength and stress-dilatancy behavior of coarse-grained soils is based on methods developed for poorly-graded sands, without explicit consideration for differences in gradation. This paper investigates the influence of the range of particle sizes on the monotonic shear strength and the stress-dilatancy response of poorly- to well-graded soils. Using the 3D discrete element method (DEM), the applicability of commonly used sand-based stress-dilatancy frameworks is assessed for a range of gradations. This DEM investigation employs clumps of spheres to accurately simulate the particle shapes on specimens with coefficients of uniformity (CU) varying between 1.9 and 6.9. These specimens were subjected to isotropically consolidated drained triaxial compression at various relative densities and confining stresses with the objective of isolating the effects of particle size distribution from those of particle shape. The peak and critical state shear strengths and the dilatancy responses of the specimens with different gradations are evaluated. For the same state parameter, the results indicate an increase in the shear strength and rate of dilation as the range of particle sizes increases. However, the critical state line shifts downward, and its slope decreases as CU is increased. The DEM results are compared to Bolton’s stress-dilatancy relationship to highlight the inadequacies of using clean sand-based frameworks in capturing the behavior of well-graded soils.