A wide range of new digital products lumped together under the category of ‘Wearables’ or ‘Wearable Technology’ raises fundamental questions about the way we think about our individual bodies and the species Homo Sapiens. This paper traces three different relationships to what are called the ‘wearables’ and extends the notion to cover all material technologies that mediate our relations between various embodied practices and the world, and beyond pure ‘hi tech’ products. Therefore, this paper develops a general cultural approach to wearables, informed by empirical examples from the US and China, and ends by mapping valuable design spaces for the next generation of digital technologies that are getting closer to our bodies and our skin, even venturing beneath it.