This thesis focuses on the late Qing imperial portraits. Examining representative photographic portraits of the Empress Dowager Cixi (1835-1908) taken by Yu Xunling (ca.1880s-1943), this thesis explores different concepts associated with portraiture, including representing the ruler's authority, individual identity and self-fashioning, and the function of the monarch's image. I discuss how Cixi's exploited photographs to convey her authority and to establish her identity as a merciful and transcendent ruler by fashioning herself as Guanyin, the Bodhisattva of Compassion. In addition, I analyze the political function Cixi's photographic portraits served when they were made into multiple copies and more widely circulated. In regard to Katharine Carl (1865-1938) and Hubert Vos's (1855-1935) oil portraits of Cixi, I investigate the particular factors that had an impact on the two foreign portraitists' portrayals of Cixi, including the interrelationships of the painters and the sitter who was also the patron, Chinese artistic conventions, and contemporary Western artistic tendencies. In particular, I elaborate upon how Cixi created and managed her image for the West through her daily interactions with Carl. I also put more emphasis on Vos's personalized portrait of Cixi, considering his ethnographic approach and the influence of Westerners' prevailing attitudes toward Cixi. Furthermore, I concentrate on one of Cixi's portraits painted by Carl to scrutinize the different aspects surrounding its public exhibition at the St. Louis World's Fair in 1904, the presentation to the United States government, and Westerners' receptions of this image. I establish the historical and political context and lay out the involved parties' intentions in displaying Cixi's portrait at the Fair. I also consider a variety of literary and visual depictions of Cixi found in the Western press at that time to examine how Westerners' reception and perception of Cixi's image was shaped and influenced by the contemporary press. By doing so, I argue that this representation of the Chinese imperial face played an important role in the communication between China and the United States, and exemplifies tensions between China and the West at turn of the twentieth century. This research on the public exhibition of Cixi's portrait in the West contributes to a relatively unexplored topic in scholarship of the Chinese art history.