This article presents the design, manufacture and testing of a capacitive pressure sensor with a high, tunable performance to low compressive loads (<10 kPa) and a resolution of less than 0.5 kPa. Such a performance is required for the monitoring of treatment efficacy delivered by compression garments to treat or prevent medical conditions such as deep vein thrombosis, leg ulcers, varicose veins or hypertrophic scars. Current commercial sensors used in such medical applications have been found to be either impractical, costly or of insufficient resolution. A microstructured elastomer film of a polydimethylsiloxane (PDMS) blend with a tunable Young’s modulus was used as the force-sensing dielectric medium. The resulting 18 mm × 18 mm parallel-plate capacitive pressure sensor was characterised in the range of 0.8 to 6.5 kPa. The microstructuring of the surface morphology of the elastomer film combined with the tuning of the Young’s modulus of the PDMS blend is demonstrated to enhance the sensor performance achieving a 0.25 kPa pressure resolution and a 10 pF capacitive change under 6.5 kPa compressive load. The resulting sensor holds good potential for the targeted medical application.