The digital economy is reshaping traditional economic models, driving profound transformations across industries. The digital transformation of retail enterprises serves as a key engine for the high-quality development of China’s economy and an essential metric for assessing the industry’s current state and future prospects. However, most enterprises remain in the early stages of digital transformation and face significant challenges. Small and medium-sized enterprises (SMEs), in particular, often lack a clear strategic direction for digital development, have limited awareness of their digital capabilities, or face substantial constraints in executing digital transformation initiatives. To accelerate the digital transformation of retail enterprises, there is an urgent need for a scientifically grounded and feasible evaluation framework. This study examines the modes and pathways of enterprise digital transformation, as well as the current landscape of digitalization in China’s retail sector. It proposes a preliminary index system for evaluating retail enterprises’ digital transformation capabilities, determines index scores through expert evaluation, and applies the analytic hierarchy process (AHP) along with the proportional distribution method to precisely assign weightings to each index. Based on these assessments, the study evaluates the digital capabilities of retail enterprises and offers targeted recommendations. The findings provide a valuable reference framework for retail enterprises seeking to assess their digital transformation progress. By leveraging these insights, enterprises can identify key areas of focus, refine their digital strategies, and enhance their transformation capabilities. Additionally, the study offers policy recommendations for government stakeholders to support and accelerate the digital transformation of the retail industry.