The resale of clothing and accessories is a phenomenon with roots going back centuries. However, little attention has been paid to the history of the thrift store and second-hand in its connection to sellers and how they have directed consumer choice towards the enhanced qualities of the garment, once detached from the connection to its original owner. Starting from the historical perspective, we focus our attention on the origin of resale and then on its recent contemporary history, particularly from 1970s onwards. In this analysis, we consider particularly relevant the narratives of sellers and buyers/consumers of second-hand fashion goods. Based on this approach, we investigate a case study of an online resale platform: Sellpy, founded in 2014 and that is pursuing an exponential plan of expansion fuelled by its parent company H & M, which bought 70% of the company in 2019. We had in mind to look at the two drivers of the fashion business—sustainability and IT—and how they support the strong growth of the second-hand market. The conclusions point out that much needs to be done in terms of sustainability within a business model that, although present since the fifteenth century, has never grown as it is growing today.