This study aims to analyze the hair styles featured in the collections from S/S season of 1995 to F/W season of 2004 both qualitatively and quantitatively by using content-analytical methods. This study was able to form a classifying system that divides hair styles into those artificial and those natural through systematic and scientific research. The resulting system, in turn, broadened the basis for understanding modern fashion and hair style expressions. In addition, by analyzing design-related characteristics, certain expressive techniques employed, and trends in detail, this study contributed to establishing the hair styles, which form part of socio-cultural phenomena, as an academic subject.