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In this workshop position paper, we exemplify and elaborate on how “Standing on the Shoulders of Giants” i.e. a turn to philosophy can be a very useful approach to move forward in our exploration of HCI. In line with the call for this workshop we suggest that the classic notion of “thought styles”, a notion originally developed and proposed by Ludwick Fleck, and later introduced to the HCI community by Janlert & Stolterman might be useful as a conceptual vehicle for further explorations. Further, we elaborate on how this notion might serve as a conceptual backbone for the development of new interactive systems. We explore this notion of ‘thought styles’ by revisiting its historical and philosophical roots, and we discuss how philosophical methods including questioning, critical discussion, rational argument, and systematic presentation in relation to ‘thought styles’ and in the context of HCI might be useful. Finally, and on a more fundamental level, we conclude our position paper by acknowledging that we have a lot to gain from further explorations at the intersection of philosophy and HCI.