Sensing pressure at the physical interface between the robot and the human has important implications for wearable robots. On the one hand, monitoring pressure distribution can give valuable benefits on the aspects of comfortability and safety of such devices. Additionally, on the other hand, they can be used as a rich sensory input to high level interaction controllers. However, a problem is that the commercial availability of this technology is mostly limited to either low-cost solutions with poor performance or expensive options, limiting the possibilities for iterative designs. As an alternative, in this manuscript we present a three-dimensional (3D) printed flexible capacitive pressure sensor that allows seamless integration for wearable robotic applications. The sensors are manufactured using additive manufacturing techniques, which provides benefits in terms of versatility of design and implementation. In this study, a characterization of the 3D printed sensors in a test-bench is presented after which the sensors are integrated in an upper arm interface. A human-in-the-loop calibration of the sensors is then shown, allowing to estimate the external force and pressure distribution that is acting on the upper arm of seven human subjects while performing a dynamic task. The validation of the method is achieved by means of a collaborative robot for precise force interaction measurements. The results indicate that the proposed sensors are a potential solution for further implementation in human–robot interfaces.