Research in digital transformation has focused on the challenges, determinants, or influencing resources, tools, and capabilities that enhance successful performance, innovation, competitive advantage, and internationalization. This paper discusses the process of digital transformation in the context of the footwear industry in Portugal, which is an interesting cluster of small and medium enterprises with a reported turnaround from traditional manufacturing targeting the domestic market to an innovative industry highly focused on export. The authors analyzed five important footwear companies ‘Made in Portugal’. The results show different stages of digital transformation, different levels of digital leadership, and different digital capabilities. The heterogeneous stage of digital maturity found has implications in the desired common positioning of the clustering-based brand ‘Portuguese Shoes’. The paper offers guidance for companies to align with the digital transformation requirements and respond to the global digital challenges, which can be transferred to other clustering industries and geographies.