From colloid suspension to particle aggregation in protoplanetary formation, electrostatic attraction and repulsion between particles is a key mechanism behind the aggregation and clustering of particles. Although most studies have focused on canonical spherical particles, it remains unclear how nonspherical and rough dielectric particles interact and whether the complicated interplay between roughness and charge distribution affects their force couplings. Here a boundary-element method model was leveraged to study electrostatic interactions between charged dielectric particles with modular, axisymmetric surface features. Charge accumulation at convex surface asperities decreases the strength of electrostatic interactions between particles, and the sensitivity of the electrostatic force to the particle surface roughness and orientation is especially apparent at small particle separations. Surface interactions between the particle near-contact regions were isolated to determine the degree that near-contact interactions dictate the relationship between the net electrostatic force and the particle roughness and orientation. A correction factor ΔF is introduced to recover higher order dielectric effects from a low order analytical model. Finally, implications of surface charge asymmetries produced for different particle orientations and surface roughnesses on the long-standing problem of triboelectrification are discussed.