But five years later she is one of the cosmetics industry's most successful entrepreneurs, creating a new skincare and make-up brand valued at £200 million.
Followers of her daily bright Instagram Stories and YouTube videos reckon she makes it look easy.
Not so, says Woodall, 58, as she tells the tale of the business, called Trinny London.
Before she launched her make-up start-up, in 2017, "all the chips were down," she recalls. "I couldn't afford to keep my house; my daughter's father had died, I was earning zero money. I had to make a decision: do I try and launch this business I'd been dreaming of, or do I go safe, and try and get a job? It was the hardest decision."
This was after Woodall had found fame with Susannah Constantine on hit BBC show What Not to Wear. "But then the jobs dried up, we were no longer flavour of the month in the UK - Gok Wan took over from us."
The pair found work on a similar TV makeover show for European media, "leaving London on Sunday night, returning on Friday, dashing around trying to make budget shows". What Woodall noticed, though, was the young make-up artists. "I'd watch them at work. And I'd always been a bathroom alchemist, mixing my own make-ups at home. Then I decided I wanted to create my own business."
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