This research reports on the design, fabrication, and multiscale mechanical characterization of flexible, planar mechanical metamaterials with tailorable mechanical properties. The tunable mechanical behavior of the structures is realized through the introduction of orthogonal perforations with different geometric features. Various configurations of the perforations lead to a wide range of Poisson’s ratios (from −0.8 to 0.4), load-bearing properties, and energy absorption capacities. The correlations between the configuration of the perforations and the auxetic response of the structures are highlighted through computational and experimental characterizations performed at multiple length scales. It is demonstrated that the local in-plane rotation of the solid ligaments in a uniaxially loaded structure is the primary factor that contributes to its strain-dependent auxetic behavior at macroscopic scales. Confinement of these local rotations is then used as a practical strategy to activate a self-strengthening mechanism in the auxetic structures. It is further shown that the fabrication of planar flexible structures with controllable Poisson’s ratios is feasible through spatial adjustment of perforations in the structure. Finally, discussions are provided regarding the practical applications of these structures for a new generation of highly energy-absorbing protective equipment.