Chester was born in Montéal, and attended Dawson College there. After graduation he spent two years at Newell & Sorrell in London and Utrecht, working on identity projects and saw the publication of his first typeface by Font Shop International. In 1995 Chester moved to Chicago to work with Rick Valicenti and eventually become a partner in his digital type foundry, Thirstype. In 2004 he decamped to New York City and formed Village with his wife and partner Tracy Jenkins. Chester's published designs have been used for branding programs -- including AT&T, Starwood Hotels, CBS Television, Nike -- as well as cultural and educational clients -- San Francisco Ballet, Columbia University Business School, the National September 11 Memorial & Museum, etc. He has created bespoke typefaces for Blackberry, Cooper Hewitt Smithsonian Design Museum, and the National Football League, amongst many others.