Compression therapy is now recognized as the main treatment for both the preventive and therapeutic care of venous disease, but its incorrect application may provoke severe injuries to the patient. Following the paradigm of e-Health, this paper presents a flexible, soft and battery-less wireless pressure sensor for the next-gen of smart/interconnected compression therapy kits. The sensor is manufactured with biocompatible latex foam and its softness reduces the risk of pressure sores. Moreover, the size of the sensor (30 mm of diameter) allows a great comfort of the user and the possibility of deploying multiple sensors in different locations of the medical treatment. The electromagnetic performance of the sensor is numerically opti- mized and experimentally validated, with a maximum achievable reading distance up to 17 cm, suitable for the requirement of through-the-bandage data reading. Finally, the pressure sensor is characterized through a preliminary mock-up emulating the compression of the bandages, demonstrating a linear correlation between pressure and tightening.