Aesthetics is essential in design practice, yet simultaneously taken for granted and under researched. In light of the expanding design space designers find themselves in due to digital technology’s pervasiveness in everyday things and environments, designers need new ways of grappling with the issue of aesthetics. There is recognition that design ideals and practices honed in different times and contexts, lead to reproducing ideas of how things are made, and how things could or should be presented for use. This paper examines notions and practices of aesthetics in digital design through conversations with practicing designers, design literature, and design experiments. We suggest that an attentiveness to aesthetic qualities in digital design sheds light on deeply embedded ideas in design which need to be addressed in emerging practices. Activating aesthetics is here proposed through shifts from stability to multistability, from visual to transient, and from extraordinariness to mundane and intimate bodily entanglements.