Medley Lecture: Trinny Woodall at Downe House  

On this day, we were delighted to host our first Medley Lecture of the year with Trinny Woodall, beauty entrepreneur, businesswoman, and former Downe House parent. The event was made even more special as some of our Upper Sixth girls had the opportunity to interview Trinny, showcasing their leadership, confidence, and insightful questioning skills.

Trinny reflected candidly on her school years, describing herself as:

Never that academic and I always felt quite stupid… I would always sit at the back of the class and I was 25 out of 26.

She recounted being placed in a lower year at a new school and spending her time making friends and discovering drama. Under the guidance of her teacher, Lord Ritchie, she thrived in drama, performing lead Shakespeare roles including Hamlet, which gave her a newfound sense of confidence.

Drama was the only thing where I felt I could do something… I was Hamlet, and I loved it.

Despite academic struggles, Trinny nurtured her ambitions. Leaving school at 16, she pursued further education while exploring her passions and discovering who she wanted to be. These formative experiences taught her resilience, self-awareness, and the importance of following one’s unique path.

Trinny first rose to fame as co-host of the BAFTA award-winning series What Not to Wear, inspiring women to embrace confidence and positive change. She shared that her toughest moments, including personal challenges and losing a business, were also her greatest teachers.

I’ve learned more from when I’ve screwed up than from when I’ve succeeded.

In 2017, she founded Trinny London, a skincare and makeup brand designed to simplify beauty for women. She explained that many women experience “consumer paralysis” at makeup counters—paralysed by choice and unsure where to start. Her goal was to make beauty simple, quick, and personalised.

Many women walk away from makeup counters paralysed by choice. I wanted to make it easy.

Drawing from her experience on makeover shows, she developed a system and algorithm based on thousands of women’s skin, hair, and eye profiles to recommend the most suitable products for each individual. Today, Trinny London has analysed over 1.2 million women, combining data with creativity to offer truly personalised beauty solutions.

Trinny spoke passionately about supporting women in business and life, emphasising the importance of resilience, self-belief, and turning adversity into opportunity. Reflecting on her own teenage years, she shared lessons learned from personal struggles, including a period of drug addiction and the subsequent journey to recovery.

If you don’t put yourself first sometimes, you lose yourself. It’s important to empower women to feel confident externally and internally.

Trinny explored generational differences and the evolving role of technology. She highlighted how younger generations have grown up immersed in the Internet and AI, while older generations experienced life before it. In her business, she actively embraces AI, encouraging her team to integrate it into their workflow to enhance efficiency, reduce repetitive tasks, and make data-driven decisions.

Understanding technology means you’re in control of what you’re doing, rather than letting it control you.

We would like to give a special mention to the Upper Sixth girls who conducted the interview with Trinny. They took the lead in preparing thoughtful, insightful questions, guiding the conversation with confidence, and engaging with Trinny in a professional and respectful manner. Their role not only made the lecture more dynamic and interactive but also showcased the leadership, initiative, and poise of our pupils—truly exemplifying the values we nurture at Downe House.