The goal of this research is to acknowledge the elements which hinder or facilitate the transition from linear to the circular economy in the textile and apparel sector in Romania by identifying current and desired interactions among the ecosystem’s stakeholders. Two strands of literature, one on circular economy and one on the textile and apparel sector, provide the theoretical background for this research. Currently, the way we design, produce, and use clothing has drawbacks that are becoming increasingly clear. The circular economy principles have the potential to transform the way textiles are produced, consumed and disposed of. More and more social entrepreneurs are pioneering the future of the apparel industry by offering sustainable solutions to tackling systemic problems. However, their efforts have to be elevated and amplified, as such to pave the way for creating business models that allow for both economic performance and social impact. A comprehensive mapping of ongoing activities and stakeholders in the textile and apparel sector in Romania is required to understand the roadblocks to industry transformation in the context of moving toward circular economy and to implement envisioned sustainable solutions. In the paper we used a database of 27 stakeholders, developed by applying the snowball method, to investigate current and future interactions between the main actors who operate in the textile and apparel sector. To meet its research objectives, the paper employed a phenomenological research design and built upon a workshop activity. First, we designed an online survey to understand the profile and knowledge of the circular economy of the stakeholders included in our database. Second, we employed the world café method to understand in depth the level of knowledge of the actors who attended the workshop on the circular economy in the textile and apparel sector. Third, we used the structural systemic constellations method in assessing the stakeholders’ current and future desired interactions. Last, we formulated conclusions and recommendations about future research needed to deepen the understanding of the circular economy in the textile and apparel sector. Findings showed that there is a vicious circle of different actions feeding isolation and preventing collaboration among stakeholders. Also, we found that there is a lack of collaborative spaces where stakeholders can meet, connect and explore the various opportunities to collaborate, and a lack of general awareness on “circular economy and textile and apparel” and its mechanisms. The intended audiences of the research are decision-makers and practitioners in the textile and apparel sector, as well as researchers focused on the circular economy.