The purpose of this research is to understand if there is a correlation between personality traits and preferred leadership style in the military. It examines the four personality traits given by Don Lowry, who created the True ColorsTM personality test, which are represented by color. This research will look into each of the four colors and examine their attributes. Furthermore, this research will look to three leadership styles: Situational, Transactional, and Transformational Leadership. Lastly, the data will be examined to understand if personality has any influence over leadership style. The research presented in this paper was gathered from peer reviewed academic journals, a True ColorsTM personality test, and a nine-question survey that is derived directly from each leadership category. The subjects represented in the quantitative analysis were from an undisclosed military installation and the persons were kept anonymous.