Various kinds of clothing characterized the fashion style during the Joseon Dynasty period. Cheollik, the oldest among traditional Korean costumes, was worn for diverse purposes by various classes and has immense historical value for its unique structure and form. This study reveals the aesthetic aspects of cheollik from the Joseon period, which upheld the spirit of consideration. It looks into the possibility of cheollik’s re-creation in light of the social/cultural background of that period. It also reviews the literature and compiles images of artifacts and relics of cheollik excavated from the tombs of its wearers during the Joseon period. The aesthetic aspects of cheollik reflect the mindset of Joseon people, as demonstrated by its diverse proportions and forms, qualities that exhibit “thinking outside the box” flexibility, and the ability to transcend conventions through free thinking and creative imagination in daily life. These are consistent with contemporary fashion trends, thus pointing to the modernity of cheollik, as exemplified by a number of design cases thus inspired. Cheollik represents the kind of beauty that resonates with contemporary individuals, showcasing the potential for historical elements to continuously transform into futuristic forms. In other words, the aesthetic value of cheollik begins with consideration and ends with creation.