This chapter shows Stitch Fix's industry case as an applied fashion application in cognitive cities. Fashion goes hand in hand with the economic development of better methods in smart and cognitive cities, leisure activities and consumption. However, extracting knowledge and actionable insights from fashion data still presents challenges due to the intrinsic subjectivity needed to effectively model the domain. Fashion ontologies help address this, but most existing such ontologies are "clothing" ontologies, which consider only the physical attributes of garments or people and often model subjective judgements only as opaque categorizations of entities. We address this by proposing a supplementary ontological approach in the fashion domain based on subjective influence networks. We enumerate a set of use cases this approach is intended to address and discuss possible classes of prediction questions and machine learning experiments that could be executed to validate or refute the model. We also present a case study on business models and monetization strategies for digital fashion, a domain that is fast-changing and gaining the battle in the digital domain.