Background
Woodall is the youngest of six children, three from her father's first marriage. Woodall's father made his fortune as a banker in London, and her brother is Mark Woodall, co-founder of climate change capital which is a merchant banking institution specialising in green energy resources. Woodall's maternal grandfather was Sir John Duncanson, controller of the British steel industry in the last two years of the war, who went on to become managing director of the British Iron and Steel Federation (BISF) in August 1945 and then managing director of Lithgows in 1949.
When Woodall was five years old, she was sent home from school after cutting off another pupil's plait. A family friend, Ronald Searle, who created the St Trinian cartoons that inspired the later films, likened her to a mischievous St Trinian girl, and the name Trinny stuck from then onwards. Woodall was educated at boarding schools from the age of six, which included Queen's Gate School in Queen's Gate, South Kensington, London. She also attended Baston School for Girls. She has described one of the boarding schools as "cruel" and "sadistic". She has connected a fear of being naked with the time she was made to stand totally unclothed in front of the other pupils as a punishment for having a water fight. Woodall also attended boarding schools in France and Germany between the ages of twelve and fifteen. During her school years, she felt overshadowed by her older sister who was the "star of the school", which prompted pupils to use Woodall to get to her sister.
Woodall started work in the financial and marketing sectors before becoming deeply involved in fashion, but was never certain about what occupation she wished to pursue. Her uncertainty prompted her to change job every two years. Some of her early jobs included taking coats at a restaurant, working as a secretary for a commodities company, aged eighteen, doing PR and using her contacts to promote her employer's restaurant, and working for Anoushka Hempel. In her marketing career, she did work for clients including Henry Dent-Brocklehurst, the owner of Sudeley Castle. She was discontented during her time working in marketing, commenting: "I wasn’t doing what I felt I should be doing, but what other people felt I should do. If you live your life like that you are never very happy." Despite working in marketing, Woodall's love for fashion was not suppressed. She would regularly customize her garments from the high street, and took to making her own fashion accessories, which she sold to Harvey Nichols and Harrods.
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