The features described herein are directed to a method and system for use in a computing environment for representing files stored in stacks by using a stack icon. The stack icon may include multiple thumbnail images as top elements, and may use common characteristics among the files to define the appearance of the stack. The system may also use metadata or file characteristics (e.g., time of last edit, size, etc.) to identify one file for top representation in the stack icon. The system may additionally include an empty stack icon, a generic stack icon, property based icons, and custom thumbnail icons.