What does it mean to wear a routine? This article explores a number of implications for the engagement of wearable fitness technology in everyday life. It straddles both a critical hermeneutic that explores the institutional prescription of wearable technology to combat the so-called “obesity epidemic” in American society, as well as a more phenomenological and experiential analysis that argues these data-driven technologies actually produce a qualitative re-engagement with social relationships. Expanding and enriching Adam Greenfield’s concept of “everyware” to describe ubiquitous technologies, this article develops the sub-variant “everywear” as a way to understand the increasing prevalence of technologies that are worn or in some way tethered to the body. Ultimately, it argues that studies of technology in everyday life must attend to a multiplicity of complex individual and institutional values and engagements. Furthermore, it suggests quantitative and qualitative modes of being operate dialectically in the production of everyday practice and experience.