This paper presents the work on six single-stringer specimens manufactured using the card-sliding technique with non-crimp fabrics and adopting a Double-Double (DD) stacking sequence. These specimens, representative of sub-structure level components, are used to investigate post-buckling and failure in aerospace structures. Two specimens maintain a constant thickness cross-section, while four are tapered, two of which incorporate a Teflon insert in the stringer flange. All specimens are tested under compression loading conditions, inducing skin buckling, skin-stringer separation, and eventual collapse. Numerical simulations are validated by experimental results and serve to analyze the specimens behavior and the failure mode. The load versus displacement curves of both experimental tests and Finite Element Method (FEM) analyses are compared, along with the out-of-plane displacement field. Subsequently, the observed failure modes are discussed, focusing on the various mechanisms that occurred and considering the impact of flanges and stiffener tapering. Both the FEM simulations and experimental tests demonstrate good agreement, with the flanges tapering revealing notable results. This offers promising evidence of a viable solution to optimize aeronautical structures and enhance resistance to skin-stringer separation.