In this chapter, we examine the use of the classic mean-risk models to evaluate the information systems projects for fashion retail supply chain management. To be specific, in light of different sources of uncertainty in the market (e.g., interest rate and consumer demand), the benefits and even costs associatedwith the implementation and operation of fashion retail supply chain management information systems are highly uncertain. As such, when the fashion retail companies evaluate these information systems projects, they have to consider both the anticipated benefits and risk. We first present two related models for conducting benefit and risk analysis, namely the classical mean-variance model, and the revised mean-semi-variance model. After that, we discuss the safety-first objective model and illustrate its relationship with the meanvariance model. Numerical examples are included to illustrate the applicability and decision making process based on the proposed models. Furthermore, the information systems portfolio related to fashion retail supply chain management is discussed.