This study has established a fashion illustration education plan using the contour drawing that fosters observational ability and enables creative drawing. This study developed two illustration curriculum proposals consisting of 15 weeks, combining literature and case studies. The researchers organized a step-by-step teaching plan that utilizes contour drawing according to the three stages of fashion illustration classes: foundation courses, general courses, and intensive courses. When the contour drawing is used at the beginning stage of the foundation courses of fashion illustration, it can be used as a technique to reduce the fear of students about practical skills, induce interest in illustration, and cultivate observation ability about objects. In general process, it is combined with various tools and coloring materials to strengthen expression power, and it is possible to produce detailed expressions and illustrations about human body and clothing. In intensive courses, it is expanded to the production of creative works with new aesthetics through digital techniques and mixed materials. As such, the contour drawing is expanded in various ways according to the learning contents and goals of each step, and is flexibly adjusted according to the learning content. Contour drawing has the effect of acquiring observation and expression ability, and it is analyzed as a technique that enables the production of creative illustration of students.