Mechanical testers have commonly been used to measure the frictional properties of socks. However, the friction values may be susceptible to the level of stretchiness of tested fabrics or human variability. Thus, the aim of this study was to propose a novel method that enables friction measurement of socks in a sock-wearing condition with less human variability effects. Five socks with different frictional properties were chosen. Three experimental ramp tests were performed with an artificial structure shaped like the foot-ankle complex (last) and a ramp tester to quantify the static coefficient of friction (COF) at the foot against sock, at the sock against an insole, and the foot wearing socks against the insole, respectively. The angle where the last slipped while the ramp surface was gradually inclined was used to compute the static COF values for each sock. The reliability was 0.99, and COF values ranged from 0.271 to 0.861 at the foot-sock interface, 0.342 to 0.639 at the sock-insole interface, and 0.310 to 0.614 in the third test. Socks with different frictional properties were successfully distinguished each other. Thus, the suggested protocol could be a reliable option for measuring the static COF values in the tension similar with it found in a sock-waring condition with reduced effects of human variability.