The proliferation of Artificial Intelligence (AI) is revolutionizing the contemporary digital landscape, influencing the way we interact with intelligent devices and systems. This contribution examines the impact of AI in the fields of fashion and design, exploring the daily interactions we establish with these technologies and providing a historical overview of their evolution, from their inception to present-day developments. It reflects on the possibility of implementing a critical and collaborative interaction with AI, highlighting case studies of fashion brands that utilize intelligent systems for the creation of resources aimed at the design of capsule collections and marketing campaigns. The focus is placed on the different approaches to intelligent systems and the diverse nature of outputs, analyzed along a material-virtual value spectrum. The aim is to emphasize the potential for establishing a new human-machine co-creation relationship, where users are not merely passive consumers but active participants, together with the systems, in a shared design space. A dialogic use, where mutual feedback exchange enables AI to lead us into a new era of creative symbiosis, where the boundaries between analog and digital are blurred, opening up new possibilities for design and fashion.