Many luxury retailers fear embracing digital touchpoints, believing it could diminish a brand’s integrity. This study explored luxury fashion brands’ transition from traditional marketing strategies into the current “digital age” and experiential economy. The research encompassed a 2-phase qualitative content analysis: Phase 1 used an inductive approach that analyzed and categorized print advertisement images from Vogue US 1980 and 2013 into 3 major categories—types of product or service, overall presentation, and overall appearance of digital content. Phase 2 consisted of a deductive approach that examined Chanel’s and Burberry’s online and social touchpoints. Findings showed that both luxury retailers understand the importance of aligning and maintaining a consistent, appealing brand image across all marketing channels to guarantee success. Marketers and managers must pay attention to the aforementioned constructs if they wish to maintain consumer brand loyalty and emotional engagement by transitioning from traditional into digital marketing strategies.