Streets are a representation of cities, and the image of a city is a reflection of its home country. Although attempts to ensure harmonious spatial and environmental developmentin Ghanaian settlements date back to the colonial era, these efforts have minimal physical manifestation in the urban fabric of the city of Accra. The Independence Arch of Ghana, an important landmark in the urban fabric and history of Accra, lacks the striking vista and approach it deserves. This paper introduces the use of fractal analysis of street edges to understand the characteristics of the John Evans Atta Mills (JEAM) High Street for developing recommendations to improve visibility along its stretch and the overall image of the city. The box-counting method with visual survey was used in research. The pertinent questions this paper seeks to address are as follows: What factors affect the visibility and imageability of JEAM High Street? What design aspects should be considered to improve urban visibility along JEAM High Street? What is the link of fractals to urban design and architecture? The paper recommends various design considerations and qualities to improve the urban visibility and imageability of JEAM High Street.