In turning, the wear control of a cutting tool benefits product quality enhancement, tool-related costs‘ optimisation, and assists in avoiding undesired events. In small series and individual production, the machine operator is the one who determines when to change a cutting tool, based upon their experience. Bad decisions can often lead to greater costs, production downtime, and scrap. In this paper, a Tool Condition Monitoring (TCM) system is presented that automatically classifies tool wear of turning tools into four classes (no, low, medium, high wear). A cutting tool was monitored with infrared (IR) camera immediately after the cut and in the following 60 s. The Convolutional Neural Network Inception V3 was used to analyse and classify the thermographic images, which were divided into different groups depending on the time of acquisition. Based on classification result, one gets information about the cutting capability of the tool for further machining. The proposed model, combining Infrared Thermography, Computer Vision, and Deep Learning, proved to be a suitable method with results of more than 96% accuracy. The most appropriate time of image acquisition is 6–12 s after the cut is finished. While existing temperature based TCM systems focus on measuring a cutting tool absolute temperature, the proposed system analyses a temperature distribution (relative temperatures) on the whole image based on image features.