For future healthcare applications, which are increasingly moving towards out-of-hospital or home-based caring models, the ability to remotely and continuously monitor patients’ conditions effectively are imperative. Among others, emotional state is one of the conditions that could be of interest to doctors or caregivers. This paper discusses a preliminary study to develop a wearable device that is a low cost, single channel, dry contact, in-ear EEG suitable for non-intrusive monitoring. All aspects of the designs, engineering, and experimenting by applying machine learning for emotion classification, are covered. Based on the valence and arousal emotion model, the device is able to classify basic emotion with 71.07% accuracy (valence), 72.89% accuracy (arousal), and 53.72% (all four emotions). The results are comparable to those measured from the more conventional EEG headsets at T7 and T8 scalp positions. These results, together with its earphone-like wearability, suggest its potential usage especially for future healthcare applications, such as home-based or tele-monitoring systems as intended.