Geological settings characterized by multiple coeval tectonic regimes provide a unique opportunity to understand complex interactions among different geodynamic processes. However, they remain comparatively less studied from an experimental point of view than areas with more simple patterns of deformation resulting from primary plate–boundary interactions. Here, we carried out analog experiments involving simultaneous shortening and orthogonal extension under different rheological conditions, including the effect of crustal inheritance. We performed brittle experiments and brittle–ductile experiments to simulate cases of “strong” and “weak” crusts, respectively. We present two types of experiments: (i) one-stage experiments with either shortening only or synchronous orthogonal shortening and stretching and (ii) two-stage experiments with a first stage of stretching and a second stage with either shortening only or synchronous orthogonal shortening and stretching. In our models, deformation is accommodated by a combination of normal, thrust, and strike-slip faults with structure location depending on boundary conditions and crustal inheritance. For brittle models, we show that the three types of structures can develop at the same time for intermediate ratios of stretching (extension) over shortening rates (1.40). For larger ratios and for the same amount of stretching, deformation is accommodated by normal faults at edges and in the center of the model as well as by conjugate strike-slip faults at the edges of the model. For brittle–ductile models, we always observe strike-slip faults that crosscut the entire model. They are associated with shortening-orthogonal thrust faults for models with low Ve/Vs and no initial extensional stage or stretching-orthogonal normal faults for models with high Ve/Vs and an initial extensional stage. Whatever the crustal strength, the past deformation history, and the stretching / shortening ratio, both normal and thrust faults remain with similar orientations, i.e., stretching-orthogonal and shortening-orthogonal, respectively. Instead, strike-slip faults exhibit orientations with respect to the shortening direction that vary between ∼0 and ∼65∘. Strike-slip faults parallel to the shortening direction develop in previously extended portions of models with a brittle–ductile crust, while strike-slip faults with a high angle form at the boundaries of the brittle model, their orientation being to some extent influenced by pre-existing or newly forming graben in the center of the model. We also show that extensional structures formed during a first stage of deformation are never inverted under orthogonal shortening but can be reactivated as normal or strike-slip faults depending on Ve/Vs. Our experiments reproduce V-shaped conjugate strike-slip systems and normal faulting during compression similar to structures observed in the Tibetan Plateau, the eastern Alps, western Anatolia, and the Central Asia orogen. Models with two-stage deformation show variable extensional to strike-slip reactivation of former extensional basins during basin-parallel shortening, which resembles synorogenic foreland transtensional reactivations documented in the Baikal and Golfo de San Jorge basins.