Today, the evolution of the textile and clothing industry has several organizational, social, qualitative and quantitative challenges arising from economic, industrial and technological changes and draconian market demands. These challenges have an impact on the implementation of an artificial intelligence system. In this context, this study aims to use the gambling and stratified sampling methods to evaluate the digital performance of five Tunisian clothing companies, with the aim of selecting the most efficient ones. We reached the following results: E1 = 49.25%, E2 = 44.25%, E3 = 45.75%, E4 = 33.75%, and that company E5 had the best score of approximately 62%, revealing a DP < 50%. While E5 achieved a DP ratio of approximately 62%, this enabled us to prepare the company to address AI technologies, such as Industry 4.0, the Internet of Things, and others, in a simple and sustainable manner. Not only that, but in this research, we also focused on six pillars (leadership, culture and organization, technology management, data management, measurement system, and customer experience). Finally, for a good digital preparation of the company, as well as to combat risk factors such as absenteeism, overall company performance, sources of non-performance, errors, omissions, defects, organizational factors, etc., this method offers the potential, along with other organizational tools, to verify their impact on the preparation of companies before implementing digital systems such as Industry 4.0 and the Internet of Things (IoT).