Although the school principal’s role has been growing in importance, the methods used to select principals have changed little since the 1950s. Moreover, researchers have seldom scrutinized principal selection methods; yet, significant procedural issues exist. The concept of fit has been used within principal selection for decades, but researchers appear to disagree on whether fit is an effective criterion and whether its use may foster discrimination. This primarily qualitative study explored the perceptions and practices of top-level district administrators regarding the use of fit within principal selection processes through a conceptual framework of cloning cultures which raise significant equity issues for non-Caucasian selection participants. Results of this study indicate participants define fit both similarly and differently, they believe fit is an important attribute sought in selection, using fit within selection has both advantages and disadvantages, and selecting principals based on fit does not guarantee that a principal will fit the school and district community. Therefore, the concept of fit should be clearly defined and operationalized. In addition, objective assessment criteria should be developed if fit is to be used within principal selection processes to promote equality within selection practices.