From 1965 to 1966 he was cartoonist and illustrator on the Sunday Mirror, and in 1966 was also one of the founder members of the British Cartoonists' Association. From 1966 to 1967 Whitford was Pocket Cartoonist on the Evening Standard, and he has been Pocket Cartoonist on the Sunday Mirror since 1969.
Whitford was also Lecturer on the History of Art at University College, London from 1970 to 1974, and at the University of Cambridge from 1974 to 1986, and was Tutor in the History of Art at the RCA from 1986 1991. Since 1991 he has been art critic of the Sunday Times, and has also presented two series of broadcasts about cartoonists for BBC Radio 4. Whitford draws in pen and ink.