“I’m always surprised by the amount of women, who as they turn 40, start to feel invisible. I’m thinking, fuck me. Why? Why do you feel invisible? Because you’ve had this shift in your life,” says Trinny Woodall one rainy July afternoon at the Trinny London headquarters in Chelsea, thus capturing the heart of this writer, who, at 38, is at the crossroads of children and career.
“By the time you are 35, your life has changed,” Woodall continues. “You are fully grown up and there are so many things that get to you, that drain you. You’ve maybe bought a house, had a kid, built a business. You’ve got responsibility. Your stress is showing on your face. You might not be exactly ageing yet, but you’re tired. So, let me give you something that you can rely on to make you feel better.”
At 61, Woodall maintains she would never let herself feel invisible. Dressed in a vest and pleated trouser co-ord and sat in her HQ’s media room, which is covered in dressing room mirrors, she speaks emphatically, emotively and without breaking eye contact. Of course, she knows a thing or two about being visible; she has been a pretty massive British TV celebrity for the best part of this century.
A quick rewind for the uninitiated: when I first moved to London in the early noughties, British culture and commerce saw eye to eye. London Fashion Week was abuzz with new names like Gareth Pugh, Ashish, Giles Deacon, and, a little later, Jonathan Anderson — all presenting pretty original visions of what people should be wearing. As a consequence, the British high street was thriving, with stores like Miss Selfridge, All Saints and Topshop taking in those visions and turning them into wearable outfits. And in the midst of all this, bringing those outfits to the UK middle class, was a TV programme called What Not to Wear presented by Woodall and fashion journalist Susannah Constantine, which ran from 2001 to 2007.
The show revolved around the duo giving fashion advice to a series of style-challenged participants, in that characteristically acerbic tone only the British can master. It was a success, averaging 4.8 million viewers and spawning a series of books, international versions and spin-offs, while Trinny and Susannah, as they’d come to be known, became household names. Even now, almost 20 years since What Not to Wear went off-air, cuts from the show crop up often on Britcore Instagram accounts as emblems of their time.
Today, Woodall is CEO of Trinny London, the digital-first beauty brand aimed at women over 35 that she founded in 2017. Making the most of her own platform and the trust she had built with her audience, she launched Trinny London’s website with a personalisation tool called Match2Me and introduced a line of modular makeup products dubbed The Stack. Now in its seventh year, the company’s product retention rate on the top four products (BFF SPF 30 Cream, The Elevator Neck Concentrate, Plump Up Peptide Serum and Bounce Back Moisturiser) is at 58 per cent (according to Woodall the industry average is 38 per cent). For the year ended March 2025, the company reported £70 million in revenue, with 25 per cent year-on-year growth.
“There are pros and cons to starting a brand as a celebrity. On the one hand, you have a built-in following. On the other, it’s harder to be taken seriously. But I was always very honest with my advice [since What Not to Wear] and that worked in my favour,” she says. And while her tone seems to have softened, the pursuit “to help people feel their best” appears unchanged. It’s a purpose Woodall says she discovered at a young age at boarding school, where she originally felt like a misfit: “I took a long time to try and think, what’s my connection to people? And I found this currency in how people put ourselves together. I would pierce people’s ears at school and help them with their outfits. I took real joy in helping them feel better about themselves. I think in life we all seek a sense of value — and it was really nice to learn I had value.”
Woodall says she had the first seeds of an idea for the brand in 2008, a little after the show stopped airing: “We were no longer flavour of the month, other people were doing the same thing. We took the format to [TV trade show] Mipcom in Cannes and 12 countries bought it. So we ended up filming a variation of the show in Poland, Israel, Australia, Scandinavia, America, India… We made over maybe 200 women in three years. And I realised when it came to skincare and makeup, all women had exactly the same problems, but the way those problems were received culturally was different in each market. So there was a gap for someone who could communicate with women across markets and ages.”
She continues: “At the same time, I was always researching skincare, because I’d had very bad acne and I started putting together my own products, using other products from my makeup bag. By 2010, I had so many women ask me where I’d bought my makeup kit and it was all the stuff I’d concocted. So then I thought, I want to make it for real.”
By that point, Constantine and Woodall had worked together for 15 years (the pair originally teamed up in 1994 to write a style column for The Daily Telegraph called ‘Ready to Wear’) and had begun to grow in different ways. “We work really well together and love each other. But we were driven by different things. I felt the need to do something that I was 100 per cent responsible for. I had been in a career for so long and then to start to be an entrepreneur — joining that mindset was a big switch. How do I manufacture makeup? How do I develop a formula? How do I do packaging? How do I get prototypes made? Where do I find the money?”
Dropping off her daughter at the school gates, Woodall met another mum, who worked in research and beauty, and they bonded over being career mums and the guilt that comes with it. The woman ended up investing in Woodall and helping her set up the business. Woodall then organised a closet sale, which helped her raise an additional sum. With the proceeds from the closet sale, her friend’s investment and the sale of her house, Woodall began work on her prototypes.
“I had a huge chart on my bathroom wall with all the colours, and I had women come in. I’d make them over with a makeup artist and we would then try to figure out why different colours suited different people. Slowly, patterns began to emerge,” she says. “By the end of that round, we had 69 SKUs. I had my packaging figured out and the formulas. It was time to start talking to people about investment.”
The entrepreneur based her five-year projections on her social media following, which had started to grow into a more beauty-oriented audience, largely due to the Instagram Live product reviews and makeup advice videos she had been posting. “I thought, what if 3 per cent of those guys buy my product? And what if I grow to 400,000 followers? I think I said, I’d make half a million the first year, four million the second year, 11 million in the third year and 25 in the fourth year. And all those projections were right. In reality, we hit £45 million in the fourth year.”
Still, it took a while to persuade investors. “I think the most challenging thing in business is learning the language of investors. People need a very methodical way of understanding your business, and you don’t want to flood them with information. I got in touch with 249 investors — there was a lot of rejection,” Woodall shares. The company declined to disclose the names or details of investors, but said Woodall “successfully secured backing from a select group of strategic early supporters”.
What advice would she give other entrepreneurs seeking investment? “Number one, I would say, don’t see the person you want the most first — practice and get mistakes out of the way with people who aren’t as important. Second, ask for feedback. Often after a pitch got rejected, I would email people and ask, ‘What didn’t you like?’ Sometimes I’d get a fobbed-off answer, and sometimes they gave valuable guidance like, ‘I don t think women over 35 are going to buy makeup online,’ or ‘You don’t have a retail plan.’ So I had to take those on board.”
Woodall built Trinny London as a digital-first brand based on personalisation, with the conviction that too many women face paralysis over choice and therefore would be easier to capture through her already existing online channels. “I like data. I want to know my customer. I have 1.6 million customers, and I know how they feel about their pigmentation or their skin. You lose sight of that with wholesale,” she says.
Trinny London launched for the first time in Liberty London in November 2023, a few months after opening its flagship store on King’s Road and six years after launch. Today, the brand can be found in over 33 retailers globally, with four core partners in Liberty London, Harvey Nichols, Fenwick and John Lewis. Direct-to-consumer (DTC) accounts for 75 per cent of revenue, while retail accounts for 25 per cent. “I think Covid helped us enter the mainstream. Our brand awareness skyrocketed, and even reached America,” she says. “They [consumers] discovered me because I was putting doggy nappies on my eyelashes [on Instagram] and I was giving them a laugh, and through that, they discovered Trinny London.”
The UK is the company s biggest market at 58 per cent, followed by Australia at 19 per cent and America at 10 per cent. “Australia is a really great market for us, in terms of DTC opportunities. And as it’s further away, we now need to think about setting a localised, separate profit and loss for that market,” Woodall says. “At the moment, we run everything from the UK, but we are considering having a local team, more people on the ground.”
On 22 August, Trinny London will be opening a pop-up store at 115 Newbury Street in Boston for six months. “In America, our brand awareness is at 9 per cent. This year’s goal is to grow it by 15 per cent. Massachusetts is our biggest state in America; we’ve had about two million orders just from Boston in the last year,” she shares. “I think it may have a little to do with the weather being similar. But mostly as a brand, we seem to be slotting quite nicely into that less-is-more philosophy of the women in that state. They still want to be themselves, just not as tired.”
Woodall’s social channels, which count over six million followers and subscribers, are bustling with serialised content franchises such as ‘Closet Confessions’, high street ‘Shop Ups’ and how-tos, each featuring characters from her everyday life such as her makeup artist, her tailor and her daughter. One that stands out is ‘Elevator Pitch’, in which aspirant female entrepreneurs are called to pitch their businesses to Woodall in 30 seconds, while riding the elevator in her company HQ.
Is she looking to expand her portfolio of businesses? “Whether it’s under Trinny London or under me, I don’t know. But I do think about what our next verticals should be. We started with makeup and now we are doing skincare. But what is the breadth of the perimeter in which you can have a customer trust you? Would anyone buy a cookbook from me? No. But would she buy things that influence how she feels about herself in other ways? Possibly.”
This tired woman is looking forward to what she comes up with next.
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