Different studies in the scientific literature have shown how the transition towards a circular economy (CE) can benefit from product design, although maintaining a rather broad and qualitative perspective of analysis. This study investigates and compares which product design strategies (from routinely design, structural optimization, industrial design and systematic innovation) are most used by students and professional designers to implement different CE strategies (i.e., waste reduction, reuse, remanufacturing, recycling and biodegradability). Students’ data were collected from year projects and MSc degree theses based on real industrial case studies and carried out in two Italian engineering universities, while those of professional designers, were collected from selected scientific articles. Among the main outcomes emerged that the design strategies deriving from systematic innovation were preferred by students quite clearly. The design strategies referred to industrial design, e.g., user-centered design and timeless design were preferred by professional designers. The design strategies related to routine design, i.e., materials substitution, reducing resources and energy consumption, and structural optimization, were indistinctly used by both students and professional designers. The obtained results and their discussion can be useful during eco-design teaching to show the main gaps that students should fill in comparison with professional designers.