Wearable piezoelectric energy harvesting offers a promising solution for powering low-power sensing modules in self-sustained health monitoring systems. In this study, we present an insole-integrated piezoelectric energy harvesting framework and experimentally evaluate the effects of transducer placement and circuit configuration under realistic gait conditions. The results reveal that DC parallel rectification provides consistently superior charging capability, whereas the EH301A energy management module enhances output stability through automated regulation. These findings establish circuit selection criteria for intermittent biomechanical excitation and highlight the feasibility of self-powered insole sensors for IoT-based wearable applications. The proposed system functions as a self-powered insole sensor that simultaneously detects plantar-pressure-induced strain and converts it into regulated electrical energy for wearable electronics, demonstrating sensing-enabled energy harvesting relevance to Smart Footwear and IoT-based health monitoring applications.