In 1991, as a riposte to red lipstick, Bobbi Brown, a then 30-something makeup artist, launched her eponymous brand with a handful of nude lipsticks. It marked the world’s introduction to the no-makeup makeup look, the antithesis of the more-is-more aesthetic that reigned in women’s makeup bags long after the 80s had made its exit.

As a jobbing makeup artist, she initially sold it directly to friends and clients and then, fortuitously, met a buyer from Bergdorf Goodman in New York, where it officially launched. Brown expected to sell 100 lipsticks a month. The new brand sold 100 a day. It outperformed all the establishment beauty brands in the store and very quickly other retailers, such as Neiman Marcus, asked to stock the brand across the country.

“I wanted women to look like they weren’t really wearing makeup,” Brown said.

Four years later, Estée Lauder Companies (owner of Estée Lauder, Jo Malone London, MAC Cosmetics, Clinique and more) came calling. Brown sold her company (for a reported $75m), stayed on as the captain of the now global Bobbi Brown ship, steering it towards becoming a billion-dollar company. And then, in 2016, she walked away. No one saw it coming.

“Burnt,” is how she describes how she felt at the time. “I was done. I thought, ‘I’ve done it, I’ve succeeded, I’ve built a billion-dollar brand, I’m done with beauty.’” Fashion and beauty history is filled with designers and founders who have put their names on a label, only for them to then have to give them up when they sell to a conglomerate. Typically, the designer themselves disappears, never to be seen again.

But not Brown. Weeks in, she realised she was not quite done. There were a number of false starts, including a short-lived supplements line (“I thought I was going to be this natural wellness guru. It didn’t happen,” she deadpans) and a futile attempt to go back to being a freelance makeup artist (“No agent wanted to represent me,” she says with a shrug.) But then she hit the jackpot – again. In October 2020, on the day her 25-year noncompete with Estée Lauder Companies ended, Brown launched Jones Road Beauty, a modern line of makeup that champions a clean minimalism.

“My philosophy with beauty,” she explains, “is about confidence and just loving what’s on your face, whether they are lines or whatever. Just go with it, it’s easier.” The brand, like its predecessor, is also fully inclusive, because, Brown says emphatically, “It’s very important to have makeup for everyone’s skin.” The timing of her launch was bold. The world was in the midst of a pandemic and, globally, makeup sales were significantly down.

And yet Jones Road tapped into the zeitgeist of what women – from TikTokers to Boomers – actually wanted. “It’s common sense,” Brown shrugs. She won’t divulge figures: “We’ve been completely profitable since day one,” is all she will say. But if the rumoured global daily sales (seven figures and counting) are anything to go by, Bobbi Brown is well on her way to creating another billion-dollar brand.

Born in 1957 to middle-class parents in the Chicago suburbs, Brown describes her mother as “beautiful and very glamorous”, but credits Ali MacGraw in “Love Story” for helping her see there was “another type of beauty”. She studied theatrical makeup at Emerson College in Boston and, after graduating in 1979, moved to New York. She contacted a makeup-artist agency and began working in the fashion industry. Eventually, she landed covers on American Vogue and Elle and grew a reputation for a minimal, nextdoor-girl aesthetic that would go on to make Brown a very rich woman, which is why the New York Times dubbed her “The Mogul Next Door.”

This no-makeup makeup look (critiqued over the years for, among other things, hiding the labour that goes into meeting Eurocentric beauty standards), involves wearing quite a lot of makeup in order to look as though you have just stepped out of a yoga class – young, fit and wealthy. This oxymoronic fashion evolved alongside Brown’s success, its most recent iteration being “clean” beauty, or the “five-minute face” – a minimalist beauty aesthetic that promises to make users look like themselves but better.

Brown’s self-assurance is light years away from the intense, fraught, blazer-and-heels woman I first met at a Bobbi Brown launch in 2015. Today, she is sitting legs folded yoga style on a banquette in Claridges, she is dressed in a low-key black sweater and jeans – and is wearing no makeup. She is diminutive – “I’m like 5ft nothing” – but on that day, she seemed towering and a little terrifying. “Yeah,” she chuckles, “there was a lot going on back then. I always had PR people staring at me; I always had marketing people around. Yes, I was in charge, but…” she adds pointedly, “I was constantly fighting for what I wanted. When I left the brand, I took off my heels and became myself again.” Leaving and being herself again meant, at 63 and in a business still rife with misogyny and ageism, Brown had to start again. “No,” she says, correcting me, “I didn’t have to start again, I chose to start again.” And rather than being intimidated by the prospect, she considered it an opportunity to do things differently. “I love a clean slate. You get to get rid of everything and think: ‘What would I do now?’”

What she has done is build a new company that is in complete contrast to her last one. No one in her team has a background in beauty. Unlike most corporate company structures, they have no CEO or COO. “We tried it, it didn’t work, we got rid of them.” Her top team is largely a family affair. There’s herself (“I have no title. I don’t need a title”); her husband, Stephen Plofker, a property entrepreneur; her son, Cody Plofker, who is the chief marketing officer; and her daughter-in-law, Payal Patel Plofker, who is the brand and marketing director. (“I actually can’t wait to go home and see my 13-month-old granddaughter,” says Brown, adding with a chuckle, “she is the child of the people who work for me, so I have an extra reason not to piss them off.”)

She and her husband live three minutes from the office and the rest of the family are also in the vicinity.

Mixing family with business seems to work well. Brown was the makeup artist for both her daughters-in-law on their wedding days. She has described it as more terrifying than being asked to do Michelle Obama’s makeup, because “I really wanted to please them.”

A self-confessed anglophile, Brown cites Soho Farmhouse in Oxfordshire, Grays Antiques Market and Anya Hindmarch’s café in London as some of her favourite haunts, and she recently joined the British Beauty Council as an ambassador. “I love the British aesthetic.” She even chose the name Jones Road, she says, because: “It sounded like a bespoke British brand that they asked me to reinvent and make more modern.”

Brown herself is a mix of modern and old-fashioned pragmatism. “Even early on in my career,” she recalls, “I would tell people how to put on makeup while trying to get their kids to school. I’d tell them to just stick to a couple of things, do them in the car at stop lights…”

Many at her namesake brand, reveals Brown, considered her everyday approach too “mumsy” or parochial. “Once, someone very high up at the old company sat me down and said: ‘I think you should buy a pied-à-terre in New York City. This way you can invite editors round and they can think you are a city girl.’ Someone else said that because I’m so small, I needed something that would make people notice me when I walked in, like a hat with a feather. Then I was told I should dress ‘cool’, so someone took me shopping for leather pants [trousers]”.

Brown can’t help the wry laugh that escapes her at the absurdity of it all. “You know, I tried all these things on, all the things you had to do to be a fancy business person, and none of it made any sense to me. Finally, I was like, ‘I think the editors liked me because we talked about normal stuff – like our kids and how tired we were.’”

While she says she loves New York, she doesn’t see herself as a “New York person” and continues to live in Montclair, New Jersey, where she moved in the late 80s with her husband.

Her authenticity, at a time when social media’s perfection is slowly beginning to lose its gloss, could explain her popularity on TikTok. When, in 2022, Meredith Duxbury, a beauty influencer known for her full-coverage makeup looks, gave Jones Road’s What The Foundation, a poor review, Brown lightheartedly parodied the influencer’s video. It went viral, resulting in a huge spike in sales. She is self-deprecating about being a social-media hit. “The joke is that afterwards I see I’ve got my hair sticking out and I’m covered in dog hair and dust. I’m like, ‘Guys, you have to tell me!’” But her fans still seem to just get it.

Brown has no plans to sell Jones Road in other stores beyond London’s Liberty, despite batting away numerous requests. Her unequivocal stance provides an insight into her success as an entrepreneur. She exudes warmth, but her eye contact is serious and unwavering; her tone direct and her vision clear. “I only launch a product when I see a need,” she says. She jokes that there is “no real strategy”, but clearly there is. Sales, she says, have “tripled” in the past year and while the company growth invariably means increased expenses, she caveats, “We do not waste money.”

And perhaps this is a clue to her success. Even her own sartorial stance has a thrifty approach – albeit a relative one. “I just like really normal things.” To my raised eyebrow she laughs and adds, “OK, yes I do like Celine [fashion designer Phoebe Philo era]. They are the things in my wardrobe I will never give away. But I’ll team it with my Uniqlo jeans.” Her penchant for Philo’s Celine – an effortless, pared-down luxe (“It would be my dream to do the makeup for her next campaign”) set the tone for the Jones Road aesthetic.

In the week we met, Philo’s highly anticipated namesake collection launched, marking her return to the industry after helming a brand that was hugely successful under her direction and walking away from it at the height of its success. Sound familiar? “I was waiting with bated breath to see what she would return with, because,” says Brown, “I love a good comeback story.”

By Funmi Fetto