While still an architecture student, Cheshire designed
Auckland restaurant, The Melba, which led to his obtaining a number of commissions for residential dwellings after he graduated. He first set up architectural collective, Artifice, with fellow young graduates, and later joined with
Pete Bossley to form Bossley Cheshire Architects in 1984. In 1989, Bossley Cheshire merged with JASMaD and Gibbs Harris to form Jasmax, of which Cheshire was a director from 1989 to 2003, the final three years managing director. From 2003, he was in practice as Cheshire Architects, alongside his son
Nat. In 2003, Cheshire was appointed adjunct professor of architecture at the University of Auckland. From 2014 to 2016, he was the national president of the NZIA. During his tenure, he worked with
Ngā Aho, the society of Māori design professionals, including
Haare Williams,
Rau Hoskins and
Elisapeta Heta, to formulate
Te Kawenata o Rata, a covenant to formalise and invigorate the relationship between the NZIA and Ngā Aho. Cheshire also served as a member of the Auckland urban design panel. In 2008, Cheshire collaborated with photographer Patrick Reynolds to produce a book on the New Zealand
bach, ''Architecture uncooked: the New Zealand holiday house through an architect's eye''. ==Death==