Sustainable apparel retailing plays a pivotal role in addressing environmental and social concerns, making it imperative to understand the challenges, leverage opportunities, and anticipate future trends in this dynamic sector. This chapter explores a comprehensive analysis of the complex landscape of sustainable apparel retail, elucidating the array of challenges, opportunities, regulatory frameworks, case studies, and future trends shaping this dynamic sector. Through an in-depth examination, it investigates the critical challenges confronting retailers, including sourcing sustainable materials, ensuring transparency and traceability in the supply chain, navigating cost implications, and reconciling sustainability objectives with prevailing fashion trends and design paradigms. Conversely, it delineates the promising avenues available to retailers, encompassing innovative strategies related to materials sourcing and manufacturing processes, strategic collaborations with sustainable fashion stakeholders, nuanced marketing and communication approaches, and introducing sustainable packaging and logistics solutions. Moreover, this chapter thoroughly examines the regulatory and certification frameworks governing sustainable apparel retailing, providing insights into prominent sustainability certifications such as Fair Trade, GOTS, and B Corp. It further delves into considerations regarding compliance with environmental and labour standards alongside pertinent legal considerations. Additionally, through a meticulous analysis of case studies and best practices, the paper illuminates’ successful initiatives in sustainable apparel retailing, drawing from exemplary endeavours by leading sustainable fashion entities and offering tailored strategies for effectively adopting sustainable practices by small- and medium-sized retailers. Lastly, this chapter casts a forward-looking perspective, elucidating emerging technologies and innovations, evolving consumer preferences, market dynamics and avenues for growth and expansion within the sustainable apparel retail sector. This study offers a robust framework for comprehensively understanding and navigating the challenges, leveraging the opportunities, and strategically positioning oneself amidst the evolving landscape of sustainable apparel retail.