In recent years, there has been an increasing interest in open-hole and filled-hole laminate failure analysis. The open and filled-hole laminate failure analysis is used in several important areas, especially in designing mechanically fastened composite joints. Various analytical, empirical, and numerical methods are available for the design of mechanically fastened composite joints. The large number of material and geometrical design variables at the preliminary design stage makes the empirical and numerical methods effortful, expensive, and time-consuming. Therefore, analytical methods are recommended over numerical and empirical methods at the preliminary design stage merely because of their simplification in calculations, making them computationally efficient. Taking this into consideration, current research presents an improvement to the analysis capabilities of the previously introduced analytical method, i.e., the coupled approach of Classical laminate theory (CLT) and Lekhnitskii solutions. These improvements include the development of failure envelops for the open-hole and filled-hole laminates, estimation of optimized filling material for attaining maximum load-bearing capacity of filled-hole laminates, and optimization of stacking sequence for maximum load-bearing capacity of open-hole and filled-hole laminates. From the failure envelop results, it was found that failure envelopes of filled-hole laminates are bigger than open-hole laminates. Furthermore, it was found that the stiffness of the filling material should be equal to the stiffness of the laminate to achieve maximum bearing strength of the filled-hole laminate. It was also demonstrated that the coupled approach of CLT and Lekhnitskii solutions may provide carpet plots that can be utilized to optimize the stacking sequence for open-hole and filled-hole laminates.