Renewable energy production has become a key research driver during the last decade. Wind energy represents a ready technology for large-scale implementation in locations all around the world. While important research is conducted to optimize wind energy production efficiency, a critical issue consists of monitoring the structural integrity and functionality of these large structures during their operational life cycle. This paper investigates the durability of a soft elastomeric capacitor strain sensing membrane, designed for structural health monitoring of wind turbines, when exposed to aggressive environmental conditions. The sensor is a capacitor made of three thin layers of an SEBS polymer in a sandwich configuration. The inner layer is doped with titania and acts as the dielectric, while the external layers are filled with carbon black and work as the conductive plates. Here, a variety of samples, not limited to the sensor configuration but also including its dielectric layer, were fabricated and tested within an accelerated weathering chamber (QUV) by simulating thermal, humidity, and UV radiation cycles. A variety of other tests were performed in order to characterize their mechanical, thermal, and electrical performance in addition to their solar reflectance. These tests were carried out before and after the QUV exposures of 1, 7, 15, and 30 days. The tests showed that titania inclusions improved the sensor durability against weathering. These findings contribute to better understanding the field behavior of these skin sensors, while future developments will concern the analysis of the sensing properties of the skin after aging.