This chapter explores the profound transformation of the retail sector, with a specific focus on the fashion industry and the evolving concept of the shopping experience. As retail sales continue to grow globally, digitalization and dematerialization are reshaping value creation, turning shopping into an immersive, multisensory, and emotionally rich experience. Consumers increasingly seek memorable encounters rather than mere transactions, shifting the focus from product acquisition to holistic, participatory experiences across both physical and digital environments. The chapter examines the rise of omnichannel strategies, the enduring role of brick-and-mortar stores, and the expansion of e-commerce, especially in the aftermath of the COVID-19 pandemic. It delves into the limitations of online retail—particularly the absence of touch—and explores how digital innovations such as XR, AR, and AI are helping to bridge sensory gaps, enhance perceived diagnosticity, and personalize shopping experiences. Finally, it presents the fashion industry as a pioneering sector in adopting XR technologies—from VTOs to immersive stores and metaverse retail—demonstrating how symbolic engagement and identity play a central role in shaping the future of retail. The chapter offers theoretical insights and practical frameworks for understanding how digital technologies redefine consumer behavior and inform the design of next-generation shopping experiences.