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The purpose of this study is to explore the emerging issue of Digital Transformation (DT) in the Greek fashion industry, which according to literature, is highly fragmented, populated by a large number of digitally immature SMEs and financially strained, even before the outburst of the COVID-19 crisis. This paper aims to explore the current level of knowledge, understanding and adoption of Digital Transformation from fashion companies in Greece, by evaluating the results of an online survey of sixty middle and top-level executives from the fashion industry. The descriptive analysis of the survey data reveals the aforementioned technology lag and -among other findings- showcases the need for a more comprehensive, efficient, structured, less fragmented and coordinated approach towards developing a digital strategy and implementation roadmap that will guide fashion companies through the harsh realities of the post-COVID19 era, as dictated and imposed by the 'next normal' for manufacturers and retailers all over the world. [ABSTRACT FROM AUTHOR]