Wearable sensing systems have recently enabled a variety of medical monitoring and diagnostic applications in wireless health. The need for multiple sensors and constant monitoring leads these systems to be power hungry and expensive with short operating lifetimes. We introduce a novel methodology that takes advantage of contextual and semantic properties in human behavior to enable efficient design and optimization of such systems from the data and information point of view. This, in turn, directly influences the wireless communication and local processing power consumption. We exploit intrinsic space and temporal correlations between sensor data while considering both user and system contextual behavior. Our goal is to select a small subset of sensors that accurately capture and/or predict all possible signals of a fully instrumented wearable sensing system. Our approach leverages novel modeling, partitioning, and behavioral optimization, which consists of signal characterization, segmentation and time shifting, mutual signal prediction, and a simultaneous minimization composed of subset sensor selection and opportunistic sampling. We demonstrate the effectiveness of the technique on an insole instrumented with 99 pressure sensors placed in each shoe, which cover the bottom of the entire foot, resulting in energy reduction of 72%% to 97%% for error rates of 5%% to 17.5%%.