In the era of the “Industry 4.0” revolution, self-adjusting and unmanned machining systems have gained considerable interest in high-value manufacturing industries to cope with the growing demand for high productivity, standardized part quality, and reduced cost. Tool condition monitoring (TCM) systems pave the way for automated machining through monitoring the state of the cutting tool, including the occurrences of wear, cracks, chipping, and breakage, with the aim of improving the efficiency and economics of the machining process. This article reviews the state-of-the-art TCM system components, namely, means of sensing, data acquisition, signal conditioning and processing, and monitoring models, found in the recent open literature. Special attention is given to analyzing the advantages and limitations of current practices in developing wireless tool-embedded sensor nodes, which enable seamless implementation and Industrial Internet of Things (IIOT) readiness of TCM systems. Additionally, a comprehensive review of the selection of dimensionality reduction techniques is provided due to the lack of clear recommendations and shortcomings of various techniques developed in the literature. Recent attempts for TCM systems’ generalization and enhancement are discussed, along with recommendations for possible future research avenues to improve TCM systems accuracy, reliability, functionality, and integration.