The purpose of this study is to analyze the effects of playful aspects through the research into characteristics and playful expressional tendency that are expressed in the contemporary fashion illustration. This study covered from 1995, the beginning point of play trend spreading, to 2006 and the fashion magazines, illustrator’s collections, and about 1800 pieces of work which have been revealed on the internet web site were collected. At the next stage, 443 pieces of work were selected by researcher for a questionnaire. As a result of the questionnaire, ultimately frequency was more than n=5, so it examined playful expression characteristics, the methods and the effects of the modern fashion illustration based on 335 pieces of work(75.6% of total sample) which were selected by the majority of expert group. It showed the biggest part of playful expression tendency in the modern fashion illustration was ‘simplification’, and second one was ‘exaggeration’. ‘Immature expression’ and ‘fantastic expression’ which are included in kidult expression were next. Hopefully, this study would be helpful for creative expression of the fashion illustration which is fit for spreading play trend in modern society.