Caulfield studied at the Chelsea School of Art in the late 1950s, and at the Royal College of Art from 1960 to 1963, where his fellow pupils included David Hockney and R. B. Kitaj. After he left he returned to Chelsea as a teacher.
In 1964 he exhibited at the New Generation show at London's Whitechapel Gallery, which resulted in him being associated with pop art.
Caulfield's paintings are figurative, often portraying a few simple objects in an interior. Typically, he uses flat areas of simple colour surrounded by black outlines. Some of his works are dominated by a single hue.
From around the mid-1970s he began to incorporate more detailed, realistic elements into his work, After Lunch (1975) being one of the first examples. Still-life: Autumn Fashion (1978) contains a variety of different styles--some objects have heavy black outlines and flat colour, but a bowl of oysters is depicted more realistically, and other areas are executed with looser brushwork. Caulfield later returned to his earlier, more stripped-down, style.
In 1987 Caulfield was nominated for the Turner Prize and in 1996 he was made a CBE.
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