Functional Near-Infrared Spectroscopy (fNIRS) is a hemodynamic modality in human cognitive workload assessment receiving popularity due to its easier implementation, non-invasiveness, low cost and other benefits from the signal-processing point of view. Wearable wireless fNIRS systems used in research have promisingly shown that fNIRS could be used in cognitive workload assessment in out-of-the-lab scenarios, such as in operators’ cognitive workload monitoring. In such a scenario, the wearability of the system is a significant factor affecting user comfort. In this respect, the wearability of the system can be improved if it is possible to minimize an fNIRS system without much compromise of the cognitive workload detection accuracy. In this study, cognitive workload-related hemodynamic changes were acquired using an fNIRS system covering the whole forehead, which is the region of interest in most cognitive workload-monitoring studies. A machine learning approach was applied to explore how the mean accuracy of the cognitive workload classification accuracy varied across various sensing locations on the forehead such as the Left, Mid, Right, Left-Mid, Right-Mid and Whole forehead. The statistical significance analysis result showed that the Mid location could result in significant cognitive workload classification accuracy compared to Whole forehead sensing, with a statistically insignificant difference in the mean accuracy. Thus, the wearable fNIRS system can be improved in terms of wearability by optimizing the sensor location, considering the sensing of the Mid location on the forehead for cognitive workload monitoring.