Under the auspices of the “body positive movement,” there has recently been an explosion of web-based content dedicated to confronting narrow Western beauty ideals that privilege the white, thin, cis-gendered and able-bodied. Body positivity challenges this exclusionary culture by encouraging the circulation of empowering body-images and advocating for the visibility of bodies that do not fit mainstream beauty norms. This dissertation is a visual and textual analysis of five English-language body positive web spaces, Herself, Stop Hating Your Body, The Body is Not An Apology, My Body Gallery and Body Revolution. Exploring site mission statements, submission guidelines, “seed images” of site creators, and participant images and stories, it maps the representational tropes that frame digital body positive practices and the ideological formations that undergird them. It reads body positivity through an interdisciplinary lens, grounding it within a history of discourses on the relationship between subjectivity, the body and its representation to address how narratives of authenticity, visibility, and embodiment are negotiated when the body is digitally performed and disseminated. This dissertation argues that ultimately, the way the body and the image operate within digital body positivity does not significantly distance the practice from the cultural formations it attempts to combat; Instead, it proposes a radical body positive to open up productive possibilities for representing embodiment in the digital age.