This paper presents a new design of a wearable plantar pressure monitoring system in the form of a smart sock for sensing abnormal relative pressure changes. One advantage of this approach is that with a battery-free design, this system can be powered solely by radio frequency (RF) energy harvested from a radio frequency identification (RFID) reader unit hosted on a smartphone of the wearer. At the same time, this RFID reader can read foot pressure values from an embedded sensor-tag in the sock. A pressure sensing matrix made of conductive fabric and flexible piezo-resistive material is integrated into the sock during the knitting process. Sensed foot pressures are digitized and stored in the memory of a sensor-tag, thus allowing relative foot pressure values to be tracked. The control unit of the smart sock is assembled on a flexible printed circuit board (FPC) that can be strapped to the lower limb and detached easily when it is not in use. Experiments show that the system can operate reliably in both tasks of RF energy harvesting and pressure measurement.