Compression therapy is widely used as the gold standard for management of chronic venous insufficiency and venous leg ulcers, and the amount of pressure applied during the compression therapy is crucial in supporting healing. A fibre optic pressure sensor using Fibre Bragg Gratings (FBGs) is developed in this paper to measure sub-bandage pressure whilst removing cross-sensitivity due to strain in the fibre and temperature. The interface pressure is measured by an FBG encapsulated in a polymer and housed in a textile to minimise discomfort for the patient. The repeatability of a manual fabrication process is investigated by fabricating and calibrating ten sensors. A customized calibration setup consisting of a programmable translation stage and a weighing scale gives sensitivities in the range 0.4–1.5 pm/mmHg (2.6–11.3 pm/kPa). An alternative calibration method using a rigid plastic cylinder and a blood pressure cuff is also demonstrated. Investigations are performed with the sensor under a compression bandage on a phantom leg to test the response of the sensor to changing pressures in static situations. Measurements are taken on a human subject to demonstrate changes in interface pressure under a compression bandage during motion to mimic a clinical application. These results are compared to the current gold standard medical sensor using a Bland–Altman analysis, with a median bias ranging from −4.6 to −20.4 mmHg, upper limit of agreement (LOA) from −13.5 to 2.7 mmHg and lower LOA from −32.4 to −7.7 mmHg. The sensor has the potential to be used as a training tool for nurses and can be left in situ to monitor bandage pressure during compression therapy.