The main objective of this study was to compare the interface pressure applied by four different compression bandages (two elastic, one inelastic, and one multi-layer system), in various static and dynamic conditions and over time. The second objective was to compare their Static Stiffness Index and their Dynamic Stiffness Index. The compression bandages were applied on 20 legs of healthy females. Interface pressure was measured at two different points of the leg (ankle and calf), at rest in two positions (standing, supine), and during walking sequences. Interface pressure depends mainly on the mechanical properties of compression devices and on the subject morphology. Both elastic and multilayer compression devices exhibited a pressure gradient loss from the ankle to the calf. Over time, pressure loss was higher for inelastic compression bandages ( p < 0.001) than for elastic and multilayer compression systems. Pressure variation from a supine to a standing position, and during walking, was higher for both inelastic bandage and multilayer system, than for elastic bandages ( p < 0.01) whatever the measurement time and the measurement point. For all compression devices, pressure variation during walking at the ankle was about 25% of the pressure variation when switching from a supine to a standing position. These results provide a better understanding of the behavior of various bandage types. The pressure variations measured during walking are lower than those obtained when the subject switches from a supine to a standing position. This study suggests that the efficacy of compression bandages relies on the interface pressure that they exert on the legs, and the capacity of the patient to walk, which activates calf muscle.