Chester's images present the complex identities, relationships, and histories of black and brown people. His love for his friends and family paired with his frustration from a lack of dignifying, multi-dimensional representations of black and brown bodies inspired him to make these images. He makes work for the invisible, the misrepresented, and the underrepresented.

Through portraiture, he illustrates his subjects as complex individuals, and creates an intimate connection between the viewer and subject. Using varying degrees of eye contact and facial expressions, viewers engage with each subject in a unique manner. Elements of each portrait are intentionally cast in shadow, distorted, fragmented, or obstructed to instill a sense of wonder and curiosity in the viewer. The lack of complete visual information in these areas represents the breadth of identities and personalities often overlooked in mainstream representations of black and brown people.

He currently lives and works in Brooklyn, New York.