Biosensors and wearable sensor systems with transmitting capabilities are currently developed and used for the monitoring of health data, exercise activities, and other performance data. Unlike conventional approaches, these devices enable convenient, continuous, and/or unobtrusive monitoring of user behavioral signals in real time. Examples include signals relative to body motion, body temperature, blood flow parameters and a variety of biological or biochemical markers and, as will be shown in this chapter here, individual grip force data that directly translate into spatiotemporal grip force profiles for different locations on the fingers and palm of the hand. Wearable sensor systems combine innovation in sensor design, electronics, data transmission, power management, and signal processing for statistical analysis, as will be further shown herein. The first section of this chapter will provide an overview of the current state of the art in grip force profiling to highlight important functional aspects to be considered. In the next section, the contribution of wearable sensor technology in the form of sensor glove systems for the real-time monitoring of surgical task skill evolution in novices training in a simulator task will be described on the basis of recent examples. In the discussion, advantages and limitations will be weighed against each other.