I have written a post where I suggest readings for those who want to go deeper into design thinking. The basic idea is to push for more grounding when it comes to design thinking by relating it to other intellectual sources. If you have an interest in a reading list, take a look. I am also looking for suggestions for more books that could take design thinking deeper.
Simon, Herbert. "The Science of the Artificial"
Simon's book is a must in the area. Unfortunately, Simon is not read carefully enough by most people who criticize him. [I have found this article by Hatchuel to be a really good help in reading Simon: Hatchuel, A. (2001). Towards Design Theory and Expandable Rationality: The Unfinished Program of Herbert Simon. In Journal of Management and Governance. Vol 5, Numbers 3-4, September, 2001.]
Rittel, Horst. (1988). “The Reasoning of Designers”,
This short paper is one of the best explanations of what design reasoning is.
Schön, Donald. "Educating the Reflective Practitioner"
I consider Schön to present the most developed design thinking philosophy and theory today. All his readings should be mandatory for anyone who engage in design thinking. But if that is too much, then this book is a good place to start.
Lawson, Bryan. "How Designers Think"
Lawson's book really helped me to form my own understanding of design. Lawson has over the years continued to publish good books on design.
Dunne, Joseph "Back to the Rough Ground"
Probably the best book ever on practical knowledge and judgment.
Krippendorff, Klaus. "The Semantic Turn -- a new foundation for design"
One of the best contemporary books on design theory.
Pye, David. "The Nature and Aesthetics of Design"
This book was first published in 1969 and is a wonderful book on the relation between craft and design, functionality and aesthetics.
Alexander, Christoffer. "The Timeless Way of Building"
Even though Alexander is more famous for his pattern language work (which is usually heavily criticized , this is the book that to me is still relevant and fundamental in its way of posing challenging questions about the purpose of design.
Borgmann, Albert. "Technology and the Character of Contemporary Life: A Philosophical Inquiry"
Of all the readings in philosophy of technology, this is the one that has influenced me the most. A wonderful critique of contemporary design and technology.
Csikszentmihalyi, M. "Flow: The Psychology of Optimal Experience"
Still one of the best and maybe only books in psychology that has direct influence on how to think about design.
Latour, Bruno. "Pandoras Hope: Essays on the Reality of Science Studies"
A book so full of great ideas that it is almost too much. Latour makes the case for reality in a way that makes sense to design theory, it is all about the particular, about here and now.
Feyerabend, P. K. (1975). Against method : outline of an anarchistic theory of knowledge.
Another book that strongly influenced me as a PhD student and I am sure that the basic message from Feyerabend still influences me. Why methods are dangerous and why there are other approaches to change is the message.
Churchman, C. West. (1971). The Design of Inquiring Systems: Basic Concepts of Systems and Organization.
This book made a huge impact on my thinking as a PhD student. Churchman asks the question how we can design a system that can produce knowledge. Design, systems and knowledge, all brought together. [A short version of Churchman's systems philosophy can be found in his book "The Systems approach"]
Kuhn, T. S. (1962) The Structure of Scientific Revolution.
Most people read this extraordinary influential book as being about science. I find the book to be possible to read as a book about design. Notion of paradigm and "normal science" are equally relevant for anyone reflecting on design thinking.
Marcuse, Herbert. "One-Dimensional Man"
All about the consequences of getting stuck in our understanding of the world, and why we have to critically break out of dominating thought figures.
Hillman, J. (1996). The Soul’s Code – In Search of Character and Calling
Another wonderful book that shows what character and calling is all about. Any designer who sees design as based on who you are as much as what you can do should read this book.
Herrigel, Eugen. (1953). Zen in the Art of Archery.
A wonderful book that examines forms of knowing that rests on character and sensibility to reality in a way that good designers should emulate.
Dewey, J. (1934) Art as Experience.
Dewey presents maybe the best foundation when it comes to understanding experience in relation to designed artifacts and systems. Also the philosophical "father" of Donald Schon.
Cross, N. (2010, reprint of 2006 book). Designerly Ways of Knowing.
An excellent book about design as a way of knowing. [A short and simple but great version of Cross's theory of design can be found in his book "Design Thinking"]
Peter-Paul Verbeek (2011) "Moralizing Technology: Understanding and Designing the Morality of Things"
A great book about how to understand designed things.
and finally some self-promotion...
Nelson, Harold & Stolterman, Erik. "The Design Way - Intentional Change in an Unpredictable World"
The 2nd edition is published by MIT Press (2012).