Located in the District of Zeyrek in Istanbul, Turkey, the İstanbul Manifaturacılar Çarşısı (İMÇ) or Manifaturacılar Retail Center İstanbul by Doğan Tekeli, Sami Sisa, and Metin Hepgüler, and the Sosyal Sigortalar Kurumu (SSK) or Social Security Agency Complex by Sedad Hakkı Eldem are regarded as two of the most prime examples representing the major shift in the development of Turkish contemporary architecture in the 1960s. As opposed to the trend of single monolithic buildings characterizing the previous era of International Style, these two complexes offered a new formal approach in which new, large building complexes were articulated into smaller fragments. Dubbed as the “small, multipart approach”, this strategy was—and is—perceived as an appropriate strategy to generate new type of architecture considered more sensitive and respectful to the smaller urban fabric of the older, traditional Turkish neighborhood as the historical context. This paper measures this very relationship between architecture and urban fabric by utilizing fractal dimension analysis to calculate the visual complexities of theİMÇ and the SSK Complexes and the urban fabric of District of Zeyrek adjacent to these two complexes, represented in the form of block plan drawings, in a comparative manner. Thus, it is possible to evaluate the formal relationship between these two complexes and the surrounding urban fabric in terms of the visual complexities in a mathematically measurable manner.