The Creative Entrepreneur - Sarah - Jane Duncanson 'Trinny' Woodall - June 2026

Jun, 1 2026

Childhood rebelliousness often creates an independent spirit as an adult and fosters strong entrepreneurial skills. That rings true for Sarah- Jane Duncanson ‘Trinny’ Woodall. She was given the nickname Trinny following an assault on a fellow pupils’ hair whom Trinny cut off their 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.

She had a good education at boarding schools but it was a hard time as it was known for being cruel and sadistic. Trinny was ridiculed and felt overshadowed by her sister who was the ‘star of the school’ which prompted pupils to use Woodall to get to her sister.

Thankfully, she grew up and became business partners with Susannah Constantine who first collaborated together in 1996 on ‘Ready to Wear’ a weekly style guide for The Daily Telegraph which ran for seven years.

Then television gave them both the breakthrough into the industry they needed with the BBC series ‘What Not To Wear’. They combined their fashion knowledge and their infamous straight-talking advice to improve the dress sense of the candidates selected for the show.

In 2002, Woodall and Constantine won a Royal Television Society Award for their work on What Not to Wear, in the category of best factual presenter. The show itself was nominated for the Features Award at the BAFTAS in both 2002 and 2003.

Woodall has also made regular appearances giving fashion and beauty advice on shows such as –

This Morning
The Today Show
The Marilyn Denis Show.

In 2017 Woodall founded direct-to-consumer cosmetics brand Trinny London.

Trinny and Susannah’s business partnership developed into the book world and have co-written numerous fashion advice books, which have sold over 3 million copies worldwide. In 2023 Woodall published the book ‘Fearless’ and an accompanying podcast of the same name.

But let’s remind ourselves of the show that opened the door into a lifelong business partnership that triggered collaborative work mixed with fun and creativity with the next generation of fashion pundits- their daughters -

Trinny is an expert at what she does. Her expertise demonstrate confidence with flair and an ability to work with others shows keen teamwork and not solely driven by a solo pursuit. Her early childhood gave a glimpse into the independent entrepreneurial woman she became.

The following website takes you to her make-up page for all the ladies wanting a super glow this summer –

https://trinnylondon.com/uk/?showCountryDialog=GB

A lesson from Trinny = never underestimate the power of your youth, always challenge yourself and do not feel undermined by those jealous of your skills in the workplace.

^Alex Ashworth Director of Creativity