Oldfield was a Barnardo boy from birth. He was then fostered by a family in Durham but when a teenager his behavior was so difficult that he had to go back to a children's home for a few years. In an interview in the Telegraph Magazine (10 April 1993) he said: "My childhood wasn't deprived and I've never claimed it was .... [Barnardos] gave me a grant to go to art school when I left teacher training college and lent me money to start in business. They were very good to me."
He was one of Diana, Princess of Wales' favorite designers. He has a stutter. He is a Fellow of Hatfield College.
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