The textile and fashion industry currently face a structural transformation driven by many factors from technology and consumer lifestyle to political intervention and regulation. This chapter reflects on the global evolution of the sector’s value chain, from production to consumption, highlighting some challenges faced in the transition from a linear model to a more circular and sustainable one. We started by assessing the importance of materials used, namely cotton and polyester, their environmental impact and current trends that promote more sustainable alternatives. After this we carried out an analysis of the landscape of global fashion retail looking particularly at the present situation of the two biggest retailers: Walmart and Amazon. The digitalization of companies is a major issue, therefore this aspect was taken into consideration particularly in retail where it stood up. After looking at production and retail on a global scale, we performed the analysis of the business models of two global brands: Zara and Shein, and their strategies. Regulatory challenges with a global impact, such as the European Green Deal and the European Strategy on Textiles and Fashion, EPR (Extended Producer Responsibility) and DPP (Digital Product Passport) are also mentioned, relating them to different aspects highlighted. This study is a reflection on the present situation and recent evolution that was used for a debate at the “Forum for Textiles and Fashion Industry in transition”, at the Global Fashion Conference 2024.