The standard experimental procedures for determining the interlaminar fracture toughness are designed for delamination propagation in unidirectional specimens. However, in aerospace structural components, delamination usually occurs between plies at different orientations resulting in different damage mechanisms which can increase the value of the fracture toughness as the delamination propagates. Generally, numerical analyses employ the value measured at the delamination onset, leading to conservative results since the increase resistance of the delamination is neglected. In this paper, the fracture toughness and the R-curves of carbon/epoxy IM7/8552 are experimentally evaluated in coupons with delamination positioned at 0°/0° and 45°/−45° interfaces using Double Cantilever Beam (DCB) and Mixed-Mode Bending (MMB) tests. A simplified numerical approach based on the Virtual Crack Closure Technique (VCCT) is developed to simulate variable fracture toughness with the delamination length within a Finite Element code using a predefined field variable. The results of the numerical analyses compared with the experimental data in terms of load-displacement curves demonstrate the effectiveness of the proposed technique in simulating the increase resistance in delamination positioned between plies at 45°/−45° interface.