The new paradigm of the 21st century demand an openly different world of formative ideologies in respect to art and design. The purpose of this study is focused on trying to comprehend aesthetic essence of clothing as an, with the investigation of artistic theories manifested by art philosophers. Art to Wear was categorized into style to understand its artistic meaning as well as to analyze its character. Upon the foundation of semiotics theory, the feature of Art to Wear and its analysis category were argued in the context of Charles Morris three dimension of semiotics analysis. The conclusion to the research is like so. The feature and analysis category of Art to Wear upon a semiotics perspective was divided into syntactic dimension, semantic dimension and pragmatic dimension. The analytical categorization upon the perspective of syntactic dimension fell into the category of topology, shape and color. The semantic dimension of Art to Wear was divided into categories of denotation and connotation. In addition, the pragmatic dimension of Art to Wear analytical categorization was divided into a delivering function and common function.