Trinny Woodall: 'I am not a bossy person, but I will never sugar-coat'
Trinny Woodall has often wondered if her moment has passed, yet her forthrightness has never gone out of fashion, writes Sarah Caden
Reflecting on the time almost 10 years ago when TV work with her sidekick Susannah Constantine switched from a flood to a trickle, Trinny Woodall asks: "And who would employ me?" She goes on: "You know, I could get a consulting for a clothing firm, but what else? It's really tricky, and people say, 'Oh but you've done so much, you can do stuff', but it is tricky to get a job when you kind of dug yourself into a rather unique hole."
Trinny doesn't sound at all distressed as she recalls this period. It's not just because, with the benefit of hindsight and the subsequent success of her make-up start-up Trinny London, she can look kindly on that time of turmoil. It's more that this is what she does.
It's not the only point in the course of the conversation that Trinny characterises herself at a crossroads. Picking yourself up and starting again is a recurring theme in her life, a form of keep calm and carry on. And she at least gives the impression of being happy to share it all, not least because, given she's in the business of asking others to bare their souls to her, she should at least give something of her stripped self in return.
She talks about her sometimes lonely childhood, her "lost" partying years, her huge success with Susannah and then the loss of that, her difficulties getting pregnant, divorce and the death of her ex-husband, her make-up idea and her recent happiness with her partner Charles Saatchi - art collector and ex-husband of Nigella - all with the same note of onwards and upwards.
"I'm tremendously forthright," Trinny says when I ask if she's bossy. "I think there's a difference between bossiness and straight-talking. I'm not bossy, but I will just never sugar-coat."
She's in Dublin for a Trinny London event that has seen hundreds of women visit a grand Georgian house, where each floor has make-up stations and make-up artists, conducting consultations and make-overs. Trinny herself has done much of the hands-on work, including the make-up of a woman who travelled up from Cork in the pouring rain, without an appointment.
"She arrived in, soaking wet," says Trinny, "saw me and said, 'Oh, I didn't know you'd be here yourself."
There is a buzz in the building and Trinny is loving it all, embracing, she admits, her new life as a beauty-business disruptor. She has always wanted, she says, to shake things up.
Trinny Woodall grew up the youngest of six children, three of whom were from her banker father's first marriage and were much older. "It wasn't that chaotic mad household you might imagine," she says. "I saw those other siblings half the time, as they were living in Canada. Also, my parents travelled a lot and when I was very young, I was at home while my siblings were at boarding school, so I was alone a lot. And then I was in boarding school from six and a half, so I did feel quite a solitary child."
Her first boarding school was "cruel", she says, adding that she was much too young to send away. "My partner is sometimes tormented by that," Trinny says of Saatchi. "He says, 'Your mother is lovely, but I can't believe she did that.'"
The second boarding school was bearable, though Trinny felt she had to live up to the reputation of her older sister, who was very bold and cool and popular.
"All the teachers thought I was going to be that naughty and all the girls thought I was going to be cool, and I wasn't. So it wasn't until she left and I was no longer in her shadow, I suppose I was about 14 or 15, that I then got comfortable in my own skin."
Her parents lived abroad at this point, in Switzerland, Germany and France, so Trinny carved out a niche for herself, picking up Benetton clothes and other unattainable European bits for her friends, whose parents were in Africa or the Far East and who never got to leave the school during term time.
Trinny started doing makeovers back then, though the idea that this could be a career wouldn't have occurred to anyone. Her father had a "huge financial crisis" when Trinny was finishing school, and that altered what might have been her expected future. Her parents had no ambition that she would have a career, she says, but no one had expected that they'd be broke.
She went to work as a secretary - "because I had no qualifications" - and threw her real energy into her social life.
"I had grown up with quite a glamorous life," Trinny says, "and then, suddenly, at 18, it was, like, not anymore. And I think I sort of sought that through partying and fast friends and being slightly glamorous and boys… and I had about 10 years of really having to get that out of my system."
It never felt like she was having a good time, Trinny says now.
"I felt like I was running in the fast lane and I couldn't stop," she says. "Outwardly, people at that time thought I was this glamorous, fun person, but inwardly, I was just crippled, with very bad acne and impostor syndrome, they call it nowadays, just feeling that one day, you'd be tapped on the shoulder and someone would say, 'I know what you're really like'."
Ultimately, at 27, Trinny tapped herself on the shoulder. She stopped drinking, though she still smokes, and decided to start her life afresh. Her friends had, to her horror, moved on. They'd been to university, started careers, boyfriends were becoming husbands - they had grown up. Trinny felt like she was still 18 and was at an absolute loss to know what to do with herself.
She had, in all that time, continued making people over. Her flat had been a focal point, where she shared her wardrobe and did friends' make-up, but that wasn't something you did as a job. So she worked as a PA, and then moved in to financial PR and then, at a mutual friend's dinner party, she met Susannah Constantine, who had a column in the Daily Telegraph and an interest in fashion.
They clicked and, later, a friend suggested that they were both at a career crossroads and should put their heads together.
The result was a shared column in the Telegraph, then some TV work, as well as an online venture, ready2wear.com, which was ahead of its time, in that it allowed women to upload their clothing specifications and virtually try on thousands of clothes that were affordable and in the shops.
Tens of thousands of women uploaded their details and used the site, but the online shopping habit had not taken off yet, and the practice didn't convert into sales. The site failed, they lost a lot of money, and, not for the first time, Trinny felt defeated.
"That failed and Susannah went off to have a baby and I was so distraught," Trinny says. "I thought, 'I'm not really employable. What can I do apart from what I've been doing and what I love?' And I went up on this retreat for a week and I just cleared my mind and for the first time in my life I learned that, instead of thinking, 'everything in front of me is s***', you just never know what promise it holds. A week later, the BBC rang to say they loved this little pilot we had done nine months earlier."
That show was What Not to Wear, a phenomenon of the Noughties that saw Trinny and Susannah achieve what seemed like world domination.
The show ran from 2001 to 2005 and it was a pre-social-media, pre-selfie sensation, in which their subjects spelt out what they hated about their clothes - which really meant themselves - and then allowed Trinny and Susannah to tough-love break them down before building them back up again into a better-dressed person with a fresh understanding of themselves. It also involved subjects standing in front of several mirrors in their underwear.
They were spectacular years, and Trinny doesn't pretend otherwise. Work was a perfect marriage of her love of fashion and her personal forthrightness - Trinny had found her niche.
Onscreen, Trinny overflowed with confidence and chutzpah, but behind the scenes, her desire to have a baby was the thing that felt out of her control. She had married businessman Johnny Elichaoff in 1999, but realised early on that getting pregnant would be difficult.
"So I started IVF, and when you do a lot of IVF, you kind of go through this thing where you feel you're never going to get pregnant but you sort of don't give up, and as long as you feel you can financially afford another round, which is expensive, you just keep going," she says. "So I did and then, you know, the last two babies, I lost them slightly late - I had to give birth to one at 18 weeks."
It was very hard, Trinny says, but she was sanguine. She became pregnant again at the start of 2003 after her obstetrician suggested they try the IUI process instead of IVF; Susannah was pregnant with her second of three children at the same time.
"We were on the red carpet at the Oscars, presenting with Diane Sawyer," Trinny recalls, "and we both started bleeding."
Her obstetrician's advice was get home, don't worry, it'll all be fine. It was fine and Trinny's daughter Lyla was born seven months later in October 2003.
"Every single week I had a scan," Trinny says, "because I was so paranoid. And then I had to have her early because she was upside down, the wrong way around and I was losing water."
But it all worked out and it must have seemed, for a while, that nothing could go wrong. In 2005, Trinny and Susannah left the BBC for ITV, where they had more freedom to pursue other ventures. Their ITV show Trinny and Susannah Undress… featured subjects stripping naked in front of each other while concealed from the viewing audience by a sheet.
Trinny loved this concept, she says now. She loved the honesty and, by her own admission, she really gets a buzz out of the process of people, sometimes literally, laying themselves bare.
"We did three years at ITV and then, they were done with us," she says. "We had started it, but by then there was Gok and Nicky Hambleton-Jones and others, and they were, like, 'Sorry, we're bored with you. Next one.'"
It was brutal, says Trinny, because as far as the optics went, as far as their audience was concerned, they were suddenly just gone. They had seven best-selling books in print and they had a 'magic' underwear business that still rolls along today, but in terms of being big hitters, it was gone in a blink. Trinny explains how they went on to produce make-over TV shows in 16 countries, but it was incredibly hard work and they both had small children at the time.
"We did that and it nearly killed us," Trinny says. "I'd gone through a period when I hadn't worried about money at all. I'd spent quite extravagantly, and then suddenly I was having to slightly worry, and also I was realising that Johnny and I were not going to last. And it felt like everything happening at once.
"I was still getting residual income from books and things like that, but I was in a house I spent too much money on. So, things were tight, and I knew in the back of my mind I'd have to sell it, but I just wasn't ready because I left my husband, and then (some time later), you know, I met Charles and I didn't want to move in with him yet and I just didn't know where I stood or what I could do next."
She and Susannah had been tied up in each other for more than a decade by now, but Trinny knew it was time for some sort of a break. Susannah, she laughs, would be happy never to work again, but Trinny has this drive. She felt compelled to do something new, but what? As she puts it, who'd have her and as what? She had painted herself into a very beautiful but specific corner.
She had two ideas, one a clothing venture with her sister, the other this stackable, cream-based make-up, which essentially she'd been cooking up and packaging for her own use for years.
Friends with money to invest recognised her passion for it and the timely nature of the product, but the timing wasn't ideal, personally, when she began trying to pull it all together.
In 2014, her ex, Elichaoff, who was reported to have had a decades-long addiction to pain medication, died when he fell from the roof of a building.
"When Johnny died," Trinny says, "that's probably when I began to most live in the moment, because even though he wasn't very well before, I never really thought that might be the outcome. So I think there was a big element of protecting Lyla, and of navigating my own life. By that stage, I'd been with my partner for two years, and we were kind of very firmly together, but I wasn't living with him. But it was just, I think, a case of really focus on every day."
That got her through what might have been the overwhelming awareness that she had, now, to be all things to her grieving daughter.
She had friends who were keen to invest in her make-up idea, who told her to park it for a while and take a less risky route after her ex's death, but Trinny felt compelled to do it. She sold a lot of her clothes and put the £60k earned into the start-up; she got investments from friends and interested parties, she rented out her big house and took a small house that she used as office and home until she moved in with Saatchi.
She launched Trinny London, a collection of stackable, creamy cosmetics, in 2017. The portability is one selling point, but so is the fact that is an almost exclusively online brand, that sees you match your skin tone, eye colour and other features on the website, much in the style of her first internet venture with Susannah, all those years ago.
People loved the product, but it's more than that, it's become about loving Trinny. She's huge on Instagram, where she is the editor and controller of her own content, free of the constraints of TV or production teams or other potential censors. And here, being "tremendously forthright" is a huge boon.
Trinny is doing better than ever, freeing herself from worry about who will employ her by becoming the boss. "A thing Charles has taught me," she says, "is you have to be there for yourself to be there for other people. And if you put somebody else before yourself, they'll always see the worst of you. Charles said: 'Don't put Lyla first, don't put me first, put yourself first, because if you are the best person you can be, Lyla will grow up with a good influence and you will be true to yourself and whoever you are with.
"That's hard," Trinny continues, "because women feel that it's a selfish thing to do, but ultimately it's not, and it took me a long time to understand that."
Not a Kardashian, and not her model sister Kendall - it seemed that Kylie Jenner might just be the also-ran of the KUWTK blended family. The canny teen spotted an endorsement niche early on, however, and turned speculation about her plump pout to her benefit with first the Kylie Lip Kit and later Kylie Cosmetics and Kylie Skin. She has a lucrative relatability and the success of her selfie-friendly make-up saw her appear on Forbes' 2019 billionaires list.
Gwyneth doesn't even need a surname at this stage, nor much of an acting career, to keep her profile up and her fortunes bolstered. Her Goop website began as a space to pick up life wisdom and beauty advice, but now it's big business, with its own health supplements, beauty products, clothing line, pop-up shops and a roadshow. Gwyneth herself is Goop's best advertisement, and, at 47, as many female actors fear invisibility, isn't afraid to enjoy the fact.
Her nude lip colour is a key bestseller in Victoria Beckham's make-up collection, though you may have to shell out for high-end tooth-whitening to pull it off as well as she does. The success of her cosmetics shows how, if you can't afford a celebrity's clothes designs, there's room for them to offer a less expensive alternative and do very well at both ends of the price spectrum. Beckham's online tutorials are also a study in aspirational yummy-mumminess.