The film Breakfast at Tiffany`s (Dir. Blake Edwards, 1961) was adapted from Truman Capote`s novella with the same title published in 1958. With the angelic beauty of the main actress Audrey Hepburn, the sentimental theme song, and also its attractive urban backdrop of the city of Manhattan, it has became one of the globally beloved nostalgic film to date, Despite its popularity, the film has received scarce academic attention. I find the primary reason in the period in which the film was produced. The films in the 1950s reflected the postwar social atmosphere in which the conservative family ideal was emphasized to reposition returning veterans in the society. The decade after the mid-1960s, on the other hand, witnessed a new era of Hollywood filmmaking, experimenting in messages, techniques, and the mode of production. However, the early 1960s, as an in-between period, has relatively been less discussed. This paper aims to redefine the films in the 1960s, and especially suggests the importance of Breakfast at Tiffany`s as one of the representative films illustrating the unique characteristics of Hollywood films at that time. Applying Walter Benjamin`s concept of the "flaneur" to understand the main characters and closely reading the way in which the film changes the narrative from the original novella, I argue that this film demonstrates the ambivalent aspect of both the conservative and renovative Hollywood in its transitional period.