The inability to accurately predict the onset of failure in modern fabric-reinforced composite materials has hindered the implementation of these materials into the mainstream applications. Excessive qualification and structural testing must be performed on composite members as a result of uncertainty in the performance of the material, resulting in significantly higher expenses associated with these materials. This situation can only be improved through the rigorous development of both improved failure and material response prediction capabilities and improved experimental verification. The current study addresses these issues, as well as explores recent developments in numerical predictions and experimental techniques. A combined numerical investigation of damage initiation mechanics and experimental verification of predicted results for a woven glass–vinyl ester composite material is performed. More specifically, 18-oz biased (5 warp/4 fill rovings) plain weave E-glass–vinyl ester laminate with warp rovings oriented in [0/90]s and [0/90/±45]s configurations are investigated. Experimental data for the E-glass–vinyl ester [0/90]s laminate is summarized in a two-dimensional biaxial failure envelope. The feasibility of using thickness-tapered cruciform specimens for generating the experimental biaxial test data is also addressed. Finally, numerical predictions of failure of the fabric-reinforced laminate are developed and compared against the experimental failure envelope for the cross-ply laminate.