The fashion industry is at a crossroads, with the rise of E-Commerce and the increasing consumer demand for sustainability reshaping the market. As digital technologies evolve, a brand that fails to monitor market tendencies and adapt to the online market’s growing acceptance and use may risk losing competitiveness. The problem is no longer how companies engage with consumers; it is also related to their capacity to accept the importance of brand equity. The value of a brand increasingly depends on its ability to act transparently, and sustainability is nowadays a key factor that impacts brand perception, especially among young individuals. This study, which analyzes the relationship between branding, sustainability, and digital transformation in the Portuguese fashion market, strongly emphasizes the crucial role of consumer engagement. It examines how managers know consumers’ expectations of ethical practices and which good practices are being adopted to reshape the textile industry’s future.