“I do feel a loser,” Anya Hindmarch exclaims. A few seconds later, she says it again. It’s discombobulating because on paper Hindmarch comes across as one of life’s clear winners.

She was a teenager when she began building her phenomenally successful handbag brand, which now has 15 stores across the world (before the pandemic and her earlier decision that shopping’s future was digital, there were 58). She’s a mother of five. She lives in Belgravia and has an estimated net worth of $21 million. She has a blonde, serene, English-rose beauty and has been happily married for 25 years. She is a CBE and has been a UK global trade ambassador.

The bag heard round the world.

Hindmarch launched a genuinely game-changing initiative with 2007’s I’m Not a Plastic Bag, a $7 tote encouraging people not to use plastic bags at the supermarket. “More than 80,000 people queued [at Sainsbury’s] in one day for it. It was phenomenal,” Hindmarch says. “When it went on sale in Tokyo I was literally locked up in the basement, there was such a stampede. In Taiwan, 30 people ended up in hospital.”

You were like the Beatles, I say. Hindmarch, 52, makes a gurgling, embarrassed noise. “It wasn’t because of me; it was because of the bag.” But she was the brains behind the bag. “Well, it hit a nerve with people wanting to do the right thing.”

Accounting Issues

It’s a characteristically modest deflection, but it still doesn’t explain why she feels a loser. That all comes down to spreadsheets. Hindmarch has just shown me one mapping the upcoming tests her youngest 17-year-old son will be taking instead of A-levels and I’m feeling guilty it never crossed my mind to do the same for my daughter’s GCSE equivalents. But then Hindmarch is famous for spreadsheeting everything from the outfits she’ll wear each day on business trips to – apparently – the choral music she wants played at her funeral.

“That’s not a spreadsheet,” she says. “I’ve just written all my favorite music on a list on my phone.” But generally, she acknowledges, squirming, her prize possession is the labeling machine her brother gave her for Christmas. “It’s so nerdy to be like that and the kids tease me for it, so I am sensitive about it – it makes me feel ashamed. But it’s the only way I can manage everything. My mental hard drive is full.”

There’s something quintessentially British about both Hindmarch and her brand – top-drawer stuff that nonetheless eschews flashiness and dislikes being seen as having tried hard. You can’t imagine, say, Donna Karan being sheepish about admitting she loves nothing more than a perfectly aligned Google Calendar, but Hindmarch finds it “embarrassing”. Nor can you imagine most designers listing their proudest achievement as “hosting a sleepover in the bed department of Peter Jones”, let alone – in an industry that equates flakiness with hipness – being “the first accessories designer to hold an on-schedule London Fashion Week show”.

Hindmarch’s designs often include a bit of humor.

It’s the same with Hindmarch’s most memorable works – the snakeskin clutch bag that looked like a Kellogg’s Corn Flakes box, the accessories inspired by the doodles on her Seventies pencil case. Witty and original, they’re creations for people who don’t want to appear slaves to fashion.

Sitting in her white-walled office in a converted brewery in south London, under a sign made from used Kellogg’s Frosties boxes that reads “Creativity will eat strategy for breakfast”, Hindmarch is wearing wide-legged (very contemporary) jeans from Raey, the Matches boutique’s in-house brand, a dark loose shirt from hipster brand Studio Nicholson and Celine shoes with a hint of heel that – again – epitomize that not-try-hard look.

“I’m not sure I can cope with anything more than jeans. I’m not sure I want to go back to all that dressing-up stuff,” she says in the soft, rapid tones of someone who’s spent a life catching planes. “It’s always lovely to do, but I think it has to be a bit more on your own terms.”

On Your Own Terms could be the alternative title for her new memoir/self-help book, If in Doubt, Wash Your Hair, designed to help other women navigate the choppy waters of career and family and social life and to quash the insecurities, which plague Hindmarch just like the rest of us.

“We’ve all suffered with doubt, whether it’s creative doubt, organizational doubt, parenting doubt – we have to accept that’s just normal. That’s why I wanted ‘If in doubt’ in the title, along with ‘wash your hair’, because it always makes people laugh when I say it, but I can’t bear my hair not being clean. It makes me feel dirty and not able to cope.”

Hold, Please

Certainly, if there’s been a period when Hindmarch needed washed hair, it was over this past year and a bit. At the beginning of 2020, the company was in the middle of launching its I Am a Plastic Bag range, totes that felt like soft cotton but were made from recycled plastic bottles. But as the world ground to a halt, everything was put on hold.

Hindmarch with David and Samantha Cameron at London’s InterContinental hotel, 2008.

Some staff were furloughed; directors took a 15 percent pay cut. Struck down with Covid herself (she caught it from someone grand, who had caught it from someone preposterously grand, but forbids me from naming names), Hindmarch was making “a thousand million decisions with a very treacly head”.

Still, with her usual doughtiness, she soldiered on, encouraging furloughed staff to become NHS volunteers and designing personal protective equipment, not to mention reusable holsters for NHS staff to carry bits and pieces such as ID cards and glasses. “We were busy and we were lucky to be busy,” she says briskly.

Wasn’t she terrified there’d be no business at the end of it all? Among luxury items, handbags took one of the hardest Covid hits, with sales falling 19 percent according to Euromonitor International. She shakes her head. “The main thing that’s really hard for business is if you’re running on a really tight cash flow and luckily we weren’t. Obviously, you were losing money through that period, so it was about preserving your cash and making sure you really batten down the hatches and come out the other end.”

Now, she says, things are looking “quite positive”. She’s certainly energetically embracing the post-Covid world. On May 17, she opened a group of shops called the Village in Pont Street, Belgravia, where she opened her original store, including a café and a shop selling the new bags. It’s there she’ll host her socially distanced book launch, treating guests to blow-dries at the pop-up hairdressers.

“I’m not sure I can cope with anything more than jeans.”

“The book has made me feel a bit exposed, putting it out there,” she says. “But after reaching that halfway point of 50, I began to think it was time to put my fears to one side and share with other women some of the things I’d learnt along the way.” But it’s far from some Superwoman, Sheryl Sandberg-like Lean In manifesto. “That wouldn’t be fair to the sisterhood,” says Hindmarch. “People always say, ‘Oh, you’ve done all this!’ But it was not always easy.”

Hindmarch’s design, as carried by Janelle Monáe at a show during Paris Fashion Week.

The book was inspired by the events of 2019, which marked the end of seven tricky years following her 2012 sale of a majority stake in the company and the appointment of an outside CEO, with Hindmarch focusing on her work as chief creative officer. Profits fell, outlets closed and eventually she decided to buy back the company and become CEO again. “I sold it because part of me felt we needed someone better than me – more experienced, with more formal training – to lead the company. By 2019, I realized that I didn’t feel that anymore. It made me realize that I knew more than I thought I did.”

Married … with Children

Hindmarch was born into a middle-class family in a pukka corner of Essex. Her father had started his own plastics business aged 18 (her brother and sister are also entrepreneurs); her mother was a French teacher. She attended a private convent school where she struggled academically, mainly because, she suspects, she’s dyslexic. “I’ve never been diagnosed with anything, but I certainly didn’t thrive in the classroom. I’m ambitious and competitive, though not in a horrible way, so that didn’t feel great. I was annoyed because I think I have a good brain and I think that probably does make you a bit more determined.”

Instead of university, she went to Florence, ostensibly to learn Italian, where she spotted a “cool leather bag I thought I could sell back home”. She had a local factory make up samples and back in the UK sold 500 via the pages of Harper’s & Queen, making almost $10,000 in profit, which she plowed back into the company.

By the time she was 24, she’d opened her own offices/shop in Walton Street in Knightsbridge. Princess Diana was a customer (later so was Kate Middleton, along with Madonna, Gwyneth Paltrow and Angelina Jolie). Soon she was exporting to the likes of Bergdorf Goodman and Barneys in New York, Isetan in Tokyo, Joyce in Hong Kong and Singapore and Bon Marché in Paris. All this, while her contemporaries were partying. “I did feel a bit lonely at times,” she says.

Princess Diana carrying one of Hindmarch’s early designs at a 1997 performance of Swan Lake.

A great fuss has always been made about Hindmarch being a Tory – again, unusual in the too-cool-for-school fashion world. She was close to the Camerons, organizing the party’s 2008 hyper-stylish Black & White fundraising ball. Today, however, she dodges politics. “I care about business being free, and I care about letting people get on with their lives. But you know what, let’s not go there,” she says firmly.

But she was a vocal Thatcherite. “Mrs Thatcher was absolutely a role model for me. I started my business at a time when the UK [could recall] three-day weeks and a slightly depressing world and suddenly there was a moment for business. A lot of people were starting at the same time and some have gone on to be really big.”

Having grown up faster than most meant she was perhaps also readier to embrace a very grown-up domestic setup. She was 25 when she met her husband, James Seymour, a businessman 12 years her senior. He was recently bereaved, his wife having died from complications following a routine operation. “I am not sure how, but I knew the instant I met him that I was going to marry him,” she writes in the book. That’s quite a thing to know. “I think it was his sense of humor, not taking himself too seriously. I thought, ‘You’re a decent man.’ ”

Still, taking on Seymour meant taking on three children aged one, three and four. “I will never forget the first time I met [them]. They were very little and they were looking just adorable in their bubble bath. Three little soft heads. I said, ‘Hi, I’m Anya,’ and after a bit James left the room and [middle child] Tia said, ‘Are you going to be our new mummy?’ It was quite transactional for them.” Wasn’t she terrified? “It just felt right. Naivety helped, but I was very aware of what I was doing. I felt a real responsibility. You couldn’t get involved in their lives without thinking, ‘Is this for me?’ Because if you weren’t committed, that would be unfair on them. But also, from my point of view, I had to think, ‘Could I manage it?’ too. Other people’s children are not uncomplicated.”

“‘Are you going to be our new mummy?’ It was quite transactional for them.”

She was also anxious about what the family of Seymour’s first wife would make of an interloper. “For James, he’d been in a happy marriage. He was used to that and he wanted to go back to that. But I think in the parents’ shoes I would have been quite worried having this 25-year-old come on the scene after just 6 months. It was very brave of them.”

But everyone – her parents, Seymour’s parents, his in-laws, the children – was determined to make it work. Hindmarch remembers how at a family confirmation, Tia, then seven, was sitting between her and Patricia [Tia’s maternal grandmother]. “Tia took my hand and put it on her lap, which was nothing unusual. But then she put her hand on her granny’s hand. And she gently brought Granny’s hand onto her lap too, and put our hands together, so that I was holding hands with Patricia. It was the most awkward and yet the most poignant moment.”

Although the children were tiny when their mother died, the oldest two remembered her. “I was very concerned they might struggle, but I hadn’t recognized that it might be harder for the one-year-old, who’d not really known his mother, but who was missing half of himself.”

Hindmarch with her husband, James Seymour, and sons.

To minimize disruption, the couple waited three years to marry, and another three before Hindmarch had her first baby, Felix (now 20). She wasn’t worried she’d love a biological child more than her adopted ones, but feared they’d feel threatened. “At moments it wobbled them and they tested me because they must have felt, ‘Will you love them more?’ But I chose those three children and I just adore them… Today we’re a very tight family and that’s probably the thing I’m proudest of.”

Yet having so many children has, she admits, at times “nearly tipped me over the edge”. So why choose such a large family? “James is the eldest of five, so even though it’s a ridiculous number of children, it felt right somehow. And I would never not want to have experienced having a child. That’s quite primal.”

Seymour joined the business, first as finance director (today he’s joint CEO), when she took her first maternity leave and they’ve worked together harmoniously ever since. “We’re the most unromantic couple ever. We’re fond of each other but we’re not soppy. I find all that a bit sicky; I’m not good at it either. James’s way of showing affection is through teasing.”

Even if Hindmarch could afford nannies and housekeepers and boarding schools, she still beat herself up about not being a perfect mother. Her first attempt to cook her future stepchildren pasta ended in them rejecting the “congealed mess” in favor of toast. It didn’t help that her mother had been a domestic paragon. “Every bowl of Brussels sprouts came with sprinkle of toasted breadcrumbs and a chive tied in a bow. I really struggled with the fact that I can’t show my creativity as a homemaker, like my mother did.”

It’s the curse, Hindmarch thinks, of her “transition generation”, most of whom had stay-at-home mothers. “It’s been a very uncomfortable place to be for us to realize you can’t do all the chores at home and work like our father did. Something has to give.”

She and James still find themselves slipping into their parents’ roles – a Damascene moment came when she realized she was writing thank- you letters on behalf of both of them, for no other reason than she’d always done so. “We’re all at the same dinner but I’ll write the letter. He would if I asked him to, but I feel I should, because that’s what a woman does, which is ridiculous. But now we both accept that that’s no longer fair and he absolutely steps up.”

Such niggles were all forgotten 12 years ago when her eldest son, Hugo, was found to have a cancerous mole on his back. “How was this fair: to lose your mother at 4 and then to get cancer at 20?” Years of surgery ensued, then just as Hugo was reaching the five-year all-clear mark, the melanoma returned. Immunotherapy and radiotherapy cleared it up, but it took a while for the family to breathe again. “When you get the call saying it’s melanoma, it’s the biggest punch in the stomach you can ever have. And then you are so scared of being punched again that you remain braced. It feels too dangerous to relax and make yourself vulnerable because you can’t take another blow like that.”

The Duchess of Cambridge carried a Hindmarch clutch to meet with Michelle Obama at Buckingham Palace in 2011.

Still, there were “silver linings” to the experience. “You really do look at some of your everyday problems and go, ‘Give them back. I’ll take them.’ You do go back to stressing about little things, but you can pull out a bit when you need to, and just go, ‘You know what? None of this matters.’ ”

Middle age has meant that more and more Hindmarch only sweats the things that really matter. She’s tired of fashion’s “subliminal body-shaming messages”, which over the years she’s absorbed. (In the book, she bewails the fact she doesn’t have skinny legs, admitting she once nearly bailed out of a holiday because she hated the way she looked in a wetsuit.) “As an industry we really have to sort this out – we can’t just be showing one type of person. It’s ridiculous. Our customer is not one type of person, so it’s just not even smart, but it’s also not right or fair. But I’ve absolutely been guilty of doing that. It’s the same conversation around race.”

She’s even more passionate about her eco-responsibilities. “You’d be surprised how many people in fashion still just don’t care,” she says, sounding the tartest she’s been all conversation. For 2020 London Fashion Week, she eschewed a launch event, instead closing her stores for three days and filling them with 90,000 used plastic bottles, the number going to landfill every 8.5 minutes. “Everyone [on staff] had to collect 500 plastic bottles. Seeing those stores filled up with empty bottles was shocking, but sometimes you need to shock people – you can’t carry on. All kids should go to landfill sites. All kids should go to recycling centers. This is our generation’s war. More and more, fashion with a purpose is my happy place.”

In a sometimes superficial industry, this self-knowledge has brought Hindmarch peace. “I’m not a look-at-me person. I’m quite shy; I’m not that outgoing person at a party. I need a lot of sleep. I love choral music. I am not cool,” she insists.

I disagree. When I get home, I immediately compile a GCSE timetable spreadsheet.

Julia Llewellyn Smith is the author of several books, including Lovestruck