The Ng-Yan-Zeng framework of fashion statement has demonstrated the linguistic structure of a fashion statement and its relationship to the abstract design elements, concrete design elements and the physical garment. The next improvement on this Ng-Yan-Zeng framework is to specify the fitness or appropriateness of the matching between fashion statement and the abstract design elements, between the abstract design elements and the concrete design elements, finally, between the concrete design elements and the physical garment. The evaluation criteria are content-sensitive, which means there will be three different criteria corresponding to three types of relationship. The analysis is primarily based on the semantic properties of the items. For example, a fashion statement consists of many attributes, and whether an abstract design element fits in this category of attributes will be measured by the semantic properties. In this case, we anticipate the fitness can be "exactly opposite to the attribute" or "totally agree with the attribute." Hence a fuzzy function can be applied to transform the semantic property into a nominal property, varying from [-1 to +1] or from "exactly opposite" to "totally agree". Once such framework was established, it is possible to measure the fitness of the fashion statement, which reflects the skill level of the fashion designers.