Historically, Jamaican women primarily of African ancestry are known to have and celebrate their voluptuous full bodies. The confidence that arises from having a bigger body size is referred to as “fluffy.” This love and acceptance for fluffiness have been a protective mechanism against the influence of the Western thin ideal. Over the past decade however, fluffy has been put to the test of time, as it has been associated with factors such as obesity, body dissatisfaction, and a host of psychological and physical comorbidities. Further, the term fluffy seems to have literally and figuratively evolved to a new body ideal known as the thick ideal in which curves are embraced and fat is distributed in the “right places,” such as hips, thighs, and buttocks. Several factors have been identified as the culprit for this body ideal, the media being one of them. While Western media is thought to be the main contributor to this transformation, the lyrics from dancehall and calypso music suggest that the local and regional media also play a major role. This chapter reviews the origins of the term fluffy and its transformation and associated negative health outcomes. Understanding its evolution is pivotal for effective health management.