Courts in personal injury, wrongful death and employment law cases encourage economic damage experts directly and indirectly to fit their economic damage appraisals closely to the facts of the specific case, which is perhaps the broadest meaning of the term “tailoring.” The purpose of this paper is to explore a number of questions about tailoring. Why are some kinds of tailoring generally accepted, frequently encountered, and appropriate, while other kinds of tailoring are encountered less often and controversial? We briefly consider some of the myriad characteristics and circumstances that could be a potential basis for tailoring. We also consider issues raised by tailoring to qualitative factors for which no numerical measure of impact is available. Finally, from our discussion of tailoring for particular variables and particular kinds of cases, we develop some generalizations about tailoring.