During the last decade, smart materials and systems have increasingly impacted several niches, including ‘one-off/limited edition experimental fashion’. As the traditional boundaries between what is art and what was not supposed to be art are now turning into osmotic membranes, we will speculatively focus on how ‘smart material systems’ are highly contributing to outline a new creative landscape full of interesting and compelling issues. Introducing three different sub-niches of experimental fashion—multi-sensory dresses, empathic dresses, and bio-smart dresses—this article outlines the emergence of a new smart design scenario. Then, we critically discuss some of the implications of the developing research in terms of design thinking and design aesthetics. This paper aims to contribute to the topic of next design scenario, demonstrating how design research is increasingly affecting the extension of human perception, emotions, and the concept of ‘almost-living’ entities, projecting towards the redefinition of relationships with materials and objects.