[1] Born with the lower half of his right leg missing, Cheshire grew up in the seaside suburb of Sumner and became a keen surfer.

[2][3] He was educated at Sumner School and Christ's College, and went on to study political science at the University of Canterbury, graduating with a Bachelor of Arts degree in 1974.

[3] In 1976, he began studying architecture at the University of Auckland, where his classmates included Mark Wigley, Jane Aimer, John Leijh, Lindley Naismith, Diane Brand, and Gill Matthewson.

[2][6] 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.

[15] In 2013, Cheshire was awarded the New Zealand Institute of Architects Gold Medal, for outstanding contributions to the practice of architecture.