Enabled by emerging wearable sensors, telemedicine can potentially offer personalized medical services to long-term home care or remote clinics in the future, which can be particularly helpful in the management of chronic diseases. The wireless wearable pressure sensing system reported in this article provides an excellent example of such an innovation, whereby periodic or continuous monitoring of interface pressure can be obtained to guide routine compression therapy, the cornerstone of chronic venous disorder management. By applying a novel capacitive, iontronic sensing technology, a flexible, ultrathin, and highly sensitive pressure sensing array is seamlessly incorporated into compression garments for the monitoring of interface pressure. The linear pressure sensing array assesses pressure distribution along the limb in a real-time manner (up to a scanning rate of 5 kHz), and the measurement data can be processed and displayed on a mobile device locally, as well as transmitted through a Bluetooth communication module to a remote clinical service. The proposed interface pressure measuring system provides real-time interface pressure distribution data and can be utilized for both clinical and selfmanagement of compression therapy, where both treatment efficacy and quality assurance can be ascertained.