This article examines the dialectic of the retail services market in the context of the evolution of the digital society and the cyclical development of the economy. Particular attention is paid to the historical retrospective of the development of trade forms and formats of retail enterprises since the 17th–18th centuries. The key stages of trade transformation are noted: from the emergence of supermarkets in the early 20th century to the development of modern formats such as hypermarkets and discounters. In addition, the evolution of domestic retail is examined, starting from the Soviet period and ending with the current state of the market, where large chains dominate. The factors influencing the choice of store format and their impact on the competitiveness of retail chains are considered.