This article reports the pressure characteristic measurement of compressed hosiery via direct and indirect methods. In the direct method, an interface sensor is used to measure the pressure value exerted on the lower limbs. In the indirect method, the necessary parameters mentioned by the cone and cylinder model are tested to calculate the pressure value. The necessary parameters involve course density, wales density, circumference, length, thickness, tension, and deformation of the compressed hosiery. Compared with the results of the direct method, the cone model in the indirect method is more suitable for calculating the pressure value because the cone model considers the change in radius of the lower limb from the knee to the ankle. Based on this measurement, the relationship among fabrication, structure, and pressure is further investigated in this study. We find that graduation is the main influence that can change the wales density. On the other hand, elastic motors directly affect the course density and the circumference of the stockings. Our reported work provides the fabrication-structure-pressure relationship and a design guide for gradually compressed hosiery.