Ski boots are known to cause vasoconstriction in the wearer’s lower limbs and, thus, cause a “cold leg” phenomenon. To address this problem, this work provides a computational framework for analysing interactions between the ski boot and the lower limb. The geometry of the lower limb was derived from magnetic resonance imaging and computed tomography techniques and anthropometric data. The geometry of the ski boot shell was obtained by means of three-dimensional computer aided design models from a manufacturer. Concerning the ski boot liner, laser scanning techniques were implemented to capture the geometry of each layer. The mechanical models of the ski boot and the lower limb were identified and validated by means of coupled experimental investigations and computational analyses. The computational models were exploited to simulate the buckling process and to investigate interaction phenomena between the boot and the lower limb. Similarly, experimental activities were performed to further analyse the buckling phenomena. The obtained computational and experimental results were compared regarding both interaction pressure and displacements between the buckle and the corresponding buckle hooks. These comparisons provided reasonable agreement (mean value of discrepancy between the model and mean experimental results in the tibial region: 20%), underlining the model’s capability to correctly interpret results from experimental measurements. Results identified the critical areas of the leg, such as the tibial region, the calcaneal region of the foot and the anterior sole, which may suffer the most due to the hydrostatic pressure and compressive strain exerted on them. The results highlight that computational methods allow investigation of the interaction phenomena between the lower leg and ski boot, potentially providing an effective framework for a more comfortable and ergonomic design of ski boots.