An iterative method and system for performing the method are described that implement a technique to fit irregularly shaped items into a defined space. In particular, one example may take the form of a method including predetermining one or more layouts for a defined space. Each layout has a plurality of shapes. The method also includes receiving a set having a plurality of items and determining one or more configurations formed by assigning to each shape in the layout an item from the set. The items match the shapes to which they are assigned. Additionally, the method includes scoring each configuration and selecting one configuration based at least in part upon the scoring.