This paper proposes a comparative historical analysis of shopping environments, focusing on the aesthetic experience they offer to the consumer and underscoring their nature as phantasmagorias. At a time when digital disruption, exacerbated by the recent pandemic, has dramatically changed social habits and the cityscape, this research aims to investigate the impact of technological and social transformations on the buyosphere and the practice of shopping. The approach's original perspective looks at the close correlation between the flâneur and the consumer, examining how retail spaces in the modern metropolis have developed. The shopping experience is shown as a social ritual with complex facets, where the urban walker and the cityscape have gradually transformed, giving symbolic meaning to architectural forms and human identities. The findings of this study call for considering the opportunities and threats of the present scenario. The shift to the virtual realm has created new forms of phantasmagoria, such as the immersive experience in the brand's universe combined with omnichannel strategies. At the same time, the “retail apocalypse” and the reduction of spaces for wandering may risk limiting social encounters, the freedom of movement, and the individual's ability to interpret urban reality, elements that once defined the practice of flânerie.