The “Calendar Painting” in the period of the Republic of China was a medium of commercial advertising, which was initially a calendar picture for products promotion. The typical images of beautiful women dressed in cheongsams depicted in the calendar paintings became the significant feature of commercial advertising at that time. Cheongsam, as a most important representative of garment for women in the period of the Republic of China, was accompanied by the changes of times of the Republic of China with its production, transformation and development. Based on the studies of calendar advertising paintings during the time of old Shanghai, this paper elaborates such as innovation of cheongsam dress style and pattern design. In the meantime, the characteristics of cheongsam design at that time, the breakthrough on traditional aesthetics for urban women and the effects to contemporary costume design from cheongsam with Shanghai style are also researched in this paper.