The focus of this chapter is how the journey is influenced by the management of digital media. For the fashion customer journey, management has to create engaging and convenient access to products while using digital data capture and customer information to create personalised fashion journeys. Machine learning, image recognition and 3D visualisation technologies provide online consumers with a smarter shopping journey such as providing advanced image/product searching and personalised styling feeds. Through customer insight analytics, online players sharpen their business decisions to offer the right products through the right channels and touchpoints. Continuing this digital theme will be a discussion of emerging digital technologies such as AI (Artificial Intelligence) and AR (Augmented Reality) as means of influencing consumer decision-making. In the fashion sector, site design and atmosphere, functionality and experience of online sites and apps, including fulfilment and back-office and delivery/returns are particularly significant at the post-purchase stage. In keeping with other sectors, the delivery, and in the case of fashion, the returns process is significant.