An automatic content styling system receives digital content, an indication of a style, and an indication of a named entity category. The occurrences of the indicated named entity category in the digital content are identified using a trained machine learning system and the indicated style is automatically applied to the identified occurrences, resulting in styled digital content. User inputs to the styled digital content are also monitored and false positives (occurrences of the indicated named entity category that were not actually the named entity category) and false negatives (occurrences of the indicated named entity category that were not identified) are identified. These false positives and false negatives are used to further train the machine learning system.