With the proliferation of Internet of Things (IoT) paradigm, wearable devices and solutions aim to resolve unmet needs from military, automotive to healthcare domains. Particularly, there are growing interests in wearable Brain Computer Interface (BCI) from both commercial and research applications. Still uphill challenges lie ahead to bring such BCI technologies to mass market due to lack of technical, usability and application aspects. To fill these gaps, this paper presents design, development and evaluation of an IoT-enabled multimodal headwear system, iMESH. Our solution senses user’s neural, physiological and physical states through direct measurements and derives health parameters. We then developed driving fatigue assessment application as exemplar to illustrate applicability and feasibility of the proposed solution. Initial results are promising and with ongoing development on methodologies, we are hoping to further develop and validate iMESH functionalities in different applications.