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To find "criteria of simplicity" was the goal of David Hilbert's recently discovered twenty-fourth problem on his renowned list of open problems given at the 1900 International Congress of Mathematicians in Paris. At the same time, simplicity and economy of means are powerful impulses in the creation of artworks. This was an inspiration for a conference, titled the same as this volume, that took place at the Graduate Center of the City University of New York in April of 2013. This volume includes selected lectures presented at the conference, and additional contributions offering diverse perspectives from art and architecture, the philosophy and history of mathematics, and current mathematical practice.