Wiley depicts his slightly larger than life-size figures in a heroic manner, giving them poses that connote power and spiritual awakening. Wiley's portrayal of masculinity is filtered through these poses of power and spirituality. In a number of his paintings, Wiley inserts black protagonists into Old Master paintings. In 2007 he reimagined Théodore Géricault's early-nineteenth-century The Charging Chasseur with a young black man in casual streetwear as the sword-wielding hussar in his painting Officer of the Hussars. Similarly, his Napoleon Leading the Army over the Alps (2005) is based on Napoleon Crossing the Alps (1800) by Jacques-Louis David, often regarded as a "masterpiece." Wiley restaged it with an African rider wearing modern army fatigues and a bandanna. Wiley "investigates the perception of blackness and creates a contemporary hybrid Olympus in which tradition is invested with a new street credibility". While creating the work Wiley attempted to use real horses to model and found that the proportions between man and horse in the original work to be unrealistic. The purpose of art during David's time was to serve as propaganda. Although seemingly naturalistic, both Wiley's and David's portraits feature rider's who are disproportionate to their steed, because "men look a lot smaller on real horses." Wiley claims to be simultaneously drawn to the illusion used in Old Masters paintings while also wanting to expose them: "The appeal, I suppose, is that, in a world so unmasterable and so unknowable, you give the illusion or veneer of the rational, of order—these strong men, these powerful purveyors of truth. And so this thing that I do is in a strange sense being drawn toward that flame and wanting to blow it out at once." His portraits are based on photographs of young men whom Wiley sees on the street. He has painted men from Harlem's 125th Street, as well as the South Central Los Angeles neighborhood where he was born. Dressed in street clothes, his models were asked to assume poses from the paintings of Renaissance masters, such as Titian and Giovanni Battista Tiepolo. Wiley describes his approach as "interrogating the notion of the master painter, at once critical and complicit". His figurative paintings "quote historical sources and position young black men within that field of power". In this manner, his paintings fuse history and style in a unique and contemporary manner. His art has been described as having homoerotic qualities. Wiley has