Experimental and numerical studies were carried out to characterize hybrid thin- and thick-ply composite laminates and assess modelling capabilities. Five different composite laminates were manufactured using a single material system with varying proportions of thin plies (0%, 50%, and 100% thin-ply). Bearing tests were performed and the results from the tests were investigated. The results showed that performance, in terms of bearing strength at onset of damage and ultimate bearing stress, increased proportionally with the increasing amount of thin plies within the laminate. Microscopic examination of the failure modes for all laminates was performed at the center of the hole to determine the dominant failure mode. The numerical investigation uses a highly detailed mesoscale model previously validated for crash simulations but never used successfully to bearing damage areas. The results showed a good correlation regarding both the load response and the morphology of damage.