Technologies for digitizing worker actions to enhance human labor tasks, mitigate accidents, and prevent disabling injuries have garnered significant attention. This study focuses on monitoring the force exerted by the fingers and developing a wearable fingertip force sensor based on a simple elliptical ring structure in conjunction with a commercially available resistive bend sensor. Resembling a ring accessory, the sensor is easy to attach and detach, and exhibits high sensitivity, with a resistance change of approximately 9% for a fingertip load of 1 N. Furthermore, to mitigate crosstalk during finger flexion, we propose a combined configuration employing this ring-shaped sensor alongside another sensor designed for measuring and rectifying finger flexion angles. Additionally, we introduce an empirically derived fitting function and a straightforward calibration procedure to extract the function’s parameters. The proposed system achieves an average RMS error of 0.53 N for force estimations of approximately 5 N, even during finger flexion and postural changes.