Continuous use of wearable robots can cause skin injuries beneath the cuffs of robots. To prevent such injuries, understanding the contact behavior of the cuff is important. Thus far, this contact behavior has not been studied because of the difficulty involved in measuring the slippage under the cuff. In this study, for the first time, the relative displacement, slippage, and interaction force and moment at the thigh cuff of a robot during sit-to-stand motion were measured using an instrumented cuff, which was developed for this purpose. The results indicated that the slippage and relative displacement under the cuff was uneven because of the rotation of the cuff, which suggests that the risk of skin injuries is different at different positions. Especially, the skin closer to the hip showed larger dynamism, with a maximum slippage of approximately 10 mm and a displacement of 20 mm during motion. Another important phenomenon was the individual difference among subjects. During motion, the interaction force, moment, and slippage of some subjects suddenly increased. Such behavior results in stress concentration, which increases the risk of skin injuries. These analyses are intended to understand how skin injuries are caused and to design measures to prevent such injuries.