While compression therapy is the cornerstone in managing leg venous disorders, the applied pressure has to be in specific ranges in order to have an effective treatment. Medical bandages and compression stockings lack an embedded pressure measurement system. The listed class of compression for medical stockings is not utterly reliable, and achieving desired pressure profiles in medical bandages is dependent solely on the bandaging skills of clinicians. Moreover, after the recipients of compression products leave medical centers, there exists no way to continuously assess the changes in sub-bandage pressure that might occur due to movements and physiological changes of the lower extremities. Thus there is a need for a valid and reliable measurement system that can be integrated into compression products for continuous monitoring of the interface pressure. In the current study, force-sensing resistors (FSRs®), which are portable, thin, flexible, low-cost, and easy-to-use sensors, were investigated. FSRs, like many other flexible resistive sensors, are known for their qualitative rather than quantitative measurements. Therefore, they should be validated for clinical use. In this study, the FSRs were first calibrated on different surfaces, including human leg, and then evaluated in measuring interface pressures in situ. The preliminary investigations showed promising results.