In this paper, a novel approach to evaluation of feature extraction methodologies is presented. In the case of machine learning algorithms, extracting and using the most efficient features is one of the key problems that can significantly influence overall performance. It is especially the case with parameter-heavy problems, such as tool condition monitoring. In the presented case, images of drilled holes are considered, where state of the edge and the overall size of imperfections have high influence on product quality. Finding and using a set of features that accurately describes the differences between the edge that is acceptable or too damaged is not always straightforward. The presented approach focuses on detailed evaluation of various feature extraction approaches. Each chosen method produced a set of features, which was then used to train a selected set of classifiers. Five initial feature sets were obtained, and additional ones were derived from them. Different voting methods were used for ensemble approaches. In total, 38 versions of the classifiers were created and evaluated. Best accuracy was obtained by the ensemble approach based on Weighted Voting methodology. A significant difference was shown between different feature extraction methods, with a total difference of 11.14% between the worst and best feature set, as well as a further 0.2% improvement achieved by using the best voting approach.