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She and Constantine worked on the show from 2001 to 2005, combining their knowledge of fashion to improve the dress sense of the candidates selected for the show.What Not to Wear made Woodall a household name, and she and Constantine became jointly known as Trinny and Susannah., fashion and make-over expert, television presenter and author.
Woodall came to prominence as co-host and fashion advisor for five series of the BBC television series What Not to Wear.
With What Not to Wear proving popular on BBC America, Woodall worked frequently as a makeover and fashion expert on The Oprah Winfrey Show with Constantine, where they gave fashion advice and tips on how to improve overall appearance, often using themselves to illustrate the guidelines.
Woodall and Constantine began their new television show, Trinny & Susannah Undress..., in 2006.
In 2007, Woodall appeared on Comic Relief Does The Apprentice in order to raise money for Comic Relief.
The Times wrote "Trinny Woodall is a prime-time star, but is proper posh with mighty connections, as demonstrated by the six-figure sums she blagged from richer friends on Comic Relief does the Apprentice." Woodall and Constantine have appeared on Parkinson three times together.
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The first two series saw them helping couples who were experiencing difficulties in their marriages, by giving advice and a fashion makeover to increase confidence.