Gear flank changes caused by wear do not only affect the dynamic behavior of gear systems, but they can also compromise the load-carrying capacity of gear teeth up to critical failure. To help avoid unintended consequences like downtime or safety risks, a condition monitoring system needs to be able to estimate the current wear during operation based on available sensor measurements. While many condition monitoring approaches in research rely on vibrational analysis with manual feature engineering, gearboxes running at slow speed do not reveal much excitation information for this purpose. We therefore introduce an approach for slow-speed gear wear monitoring that is based on the dynamic gear transmission error and that contains an automated feature selection process. For this purpose, we extract a large set of features from the preprocessed transmission error samples. Applying combined filter and embedded feature selection methods enables us to automatically identify and remove features with low relevance. The selection process consists of filtering features with no statistical dependence on the target wear value, removing redundant features with a correlation analysis and a recursive feature elimination process with cross-validation based on a random forest regressor. The remaining relevant set of features is the basis for model training and subsequent wear estimation. For this, the present research employed two independent ensemble models, random forest regression and gradient boosted regression trees. To train and test the proposed approach, we conducted slow-speed gear experiments with developing gear wear on a single-stage spur gear test rig setup. The results of both models show good gear wear estimation performance compared to the actual wear mass loss, even for small quantities. Hence, the proposed transmission error-based approach with automated feature selection is able to quantify the degree of slow-speed wear and offers a possible way for condition monitoring and fault diagnosis.