An Atlanta native, Chester attended The Galloway School, then studied ceramics and printmaking at Penland School of Craft in North Carolina. During his tenure at Penland, Chester founded a ceramic design studio. By the age of 19, he was exhibiting his work throughout the eastern United States.
Chester received a BFA from the Atlanta College of Art (now SCAD), where he started to explore mixed media, incorporating unusual material into his conceptual installations. After he graduated from ACA he started his mixed—media studio, W.Chester Old Inc., producing innovative furniture and accessories for the home, selling to and creating work for clients throughout the U.S., Canada, and Europe.
In 2005 Chester began developing a new body of work that examined conceptual ideas he experimented with during his under graduate studies. The result, the ‘Dysfunctional Objects' and ‘Shadow Portraits’ series, continues to engage his curiosity.
Throughout his career, Chester has been the recipient of a number of prestigious awards and grants. He has appeared on numerous television shows and in many publications, and has served often as a juror for the American Crafts Council. His work continues to be exhibited in many prominent venues.