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Purpose This paper aims to analyse how sustainable second-hand stores (SSHSs) use storytelling as a legitimization strategy. Second-hand stores have traditionally relied on a charity identity to attract customers. More recently, changing market demands, the growing popularity of second-hand shopping, “vintage” and online shopping have opened up new opportunities for these social enterprises (SEs). This study asks how SSHSs can maintain their legitimacy with incumbent stakeholders while also exploiting these new opportunities. Design/methodology/approach This paper uses an abductive approach starting from existing knowledge on how storytelling builds legitimacy in conventional enterprises. The authors collected qualitative data and interviewed owners and managers of second-hand stores in the Netherlands. This paper specifically looked at how second-hand stores are using their web shops to convey stories and build legitimacy with (new) audiences. Findings Contrary to the authors’ expectations, they found that the web shop is not used as a site for storytelling the mission of the store but is rather a stage for specific products that tell a story of trendy and vintage shopping. This attracts a new customer segment to the store that conventionally does not shop there. This paper concludes that second-hand stores use vintage products as symbols in storytelling through their web shop to gain access to a new market. By foregoing to tell the story of their mission on the web shop, the second-hand stores are choosing to keep their charity and business identity separate. Originality/value To the best of the authors’ knowledge, this paper makes an original contribution by analysing how second-hand stores are actively exploiting new opportunities created by a changing market context and seeking to maintain legitimacy while doing so. This paper argues that legitimacy is not a static “reward,” rather, something that evolves with the enterprise. This research adds to the body of literature on legitimacy and more specifically cultural entrepreneurship, which holds that entrepreneurs can actively gain and maintain legitimacy through storytelling.