Bobbi Brown has always been pragmatic about beauty, with the air of a mom who tells you with no-duh confidence that yes, you would look better if slouched less, and used a little blush on your face. The only contour she likes, she tells me, is Spanx for her middle (even though a makeup artist once told her, “You’re never going to work if you don’t learn how to contour”), and she made a blue eye shadow only once (it didn’t sell well). Common sense and simplicity were at the core of her namesake brand—with its array of nudes, pinks, and beiges—and her nine books that explained that makeup was not rocket science.
The nude-makeup-loving Brown actually went to college to study theatrical makeup and photography, worked on her first film set, and quickly discovered that keeping track of bruise makeup continuity wasn’t for her (“So boring,” she says). She moved to New York City and became a freelance editorial makeup artist. Early photos from her career show her and her full 5’0 height standing on an apple box while peering thoughtfully into the faces of models like Carla Bruni. She worked with photographers like Bruce Weber and Patrick Demarchelier, who preferred a natural look to the ’80s makeup of the time (although as she tells it with her trademark mix of candor and humility, it was “because I was easy to work with, and I always showed up”).
Her editorial dreams changed as she “moved to New Jersey, got married, got pregnant, and needed money to pay the mortgage.” She did catalogs because she didn’t want to sit at shoots till 11:30 at night, and editorial didn’t pay. “You weren’t considered cool and fashion-y if you wanted to leave work at 6:00, and [had] a baby, and a husband. I always had FOMO when I saw beautiful things and trips that I didn’t go on, and was on hold for [certain jobs],” she says.
But she went a different way, becoming one of the first makeup artists to have her own line, and in 1995, she sold her company to The Estée Lauder Companies (she named her boat “TYLL”: Thank You Leonard Lauder). She continued to run the brand, and you could find a Bobbi Brown Highlighter Shimmer Brick from New York City to Kazakhstan. But as she’s sitting in front of me, in black leggings and a fanny pack (the last time I saw her, she was wearing a black blazer with shiny buttons and tailored jeans), Brown’s tenor voice and steady brown eyes don’t falter as she tells me about how unhappy she became over time. “There was marketing and products that I didn’t really believe in, but…was told were necessary.” And so she left, going down the elevator, leaving the office that bore her name for the very last time, thrilled initially about her open calendar which was normally planned two years out, but worrying about what to give away for Halloween (she used to give away away full-size beauty products like they were candy bars) and what would come next.
Bobbi calls leaving Bobbi a “loss.” She didn’t go to therapy, but she did have a chiropractor who did energy release, and a yoga instructor who was also a life coach. She became a certified health coach herself, started a wellness line, and designed and renovated a hotel, The George, with her husband, Steven Plofker. But not too long after, just as when she came up, more-theatrical beauty techniques like “baking” and contouring became popular again, leading to the ubiquity of “Instagram face”—and directly opposing Brown’s forever ethos of natural-looking makeup. She began to feel she “just wasn’t done” with beauty. “I wanted to teach women how you don’t need to do all that,” she says. She started to wear an amulet around her neck engraved with “10/20”: the month and year her 25-year noncompete agreement ended.
Jones Road, named after a street she got lost in near her Hamptons retreat, launched on October 26, 2020. She is a 66-year-old female founder—again, a double rarity in the business world. “It’s important for people to hear [about what I’m doing], because you just usually hear of people going away when they’re in their fifties, let alone sixties. They just go away,” she says from her Jones Road complex in Montclair, New Jersey.
Jones Road’s branding is glossy, no-makeup-makeup pretty, with an actual girl-next-door quality to it (Brown’s models include a hostess at a restaurant she frequents, and a stranger she saw at a farmers’ market, who is now is signed with a modeling agency). The products are tightly curated and definitively named—The Eye Pencil, The Bronzer, The Mascara—leaving little room for a marketing person to eventually say, “But what if we want to launch a different kind of Eye Pencil in time for Christmas shoppers?”
Gloria Steinem, a friend (they met at a White House event during Obama’s term), is wearing a Jones Road Miracle Balm blush when we Zoom to talk about their friendship. “She’s come into a field that was legendary for its mystique and false promises. The promise of cosmetics has often been beauty, youth, or being like the movie star who is doing the advertising. She reversed that and has redone it so that it is understandable to all consumers. That’s not easy, because tradition was against her.” When I visit Montclair, the Jones Road store is extremely busy on a Thursday afternoon; mothers are making appointments for their daughters’ prom makeup, and a customer is hugging her favorite sales associate for getting promoted to manager.
If the path to her second-time-around success seems smooth, there is also her chief marketing officer, who isn’t always fond of Brown’s ideas. “He’s the one guy who says, ‘Oh, that’s just old school,’ or ‘We don’t need that.’” He urged her to get onto TikTok, where one of the most popular beauty influencers is 22-year-old Alix Earle. “Will I look stupid?” Brown worried. “Will I look bad?” Instead, TikTok’s 30- to 50-plus demographic has found her to be a living Google, asking her questions like “What kind of makeup should I do for hooded eyes?” and “How do I do makeup in my fifties?” Brown’s beauty-for-the-real-world message has surprisingly found its perfect medium, on an app known for its beauty filters. She’s now even done a Hamptons house tour with Caleb Simpson, a creator who starts his popular videos with, “How much is your rent?” (She owns).
One of her products, What The Foundation (WTF), even went viral after maximalist beauty influencer @MeredithDuxbury spackled the tinted moisturizer over her face and declared that it wasn’t for her. Brown lovingly shaded her: “I love learning new makeup techniques, but hmm, this didn’t really work,” Brown said in her own video, giggling as she engulfed her face with WTF. The internet loves some well-placed shade, and her business quadrupled after the clip received 20 million likes. It increased again after she appeared on CBS Saturday Morning. “We had a giant spike on our sales that day, from old-fashioned TV. And then [our CMO] was like, ‘All right, Mom, you were right.’” Her CMO doesn’t call her “Mom” in a slang Gen-Z term of admiration, he is actually her son, Cody.
There are makeup artists who can transform a face, create a fantasy, and use the tricks of the trade to turn a mother into Marlene Dietrich or create definitive looks for every decade of a pop superstar. One of Brown’s gifts is that she’s always been able to see people just as they are. “It took a while [for me] to [feel] comfortable,” she says. Early in her career, Brown would do a model like Yasmeen Ghauri or Cindy Crawford, show them their finished makeup in the mirror, ask “What do you think?” and watch as they fixed it in front of her. She learned from seeing how other people wanted to be seen. “I’ve always been someone that I don’t look and see what’s wrong on a person’s face and try to fix it. I see what’s right and bring it out. When people get their makeup done at Jones, they look like themselves. When you put it on and you’re like, ‘Okay, that’s what Bobbi meant.’ ”
It seems customers are understanding Bobbi perfectly, and in just a few years, Jones Road is well on its way to becoming a billion-dollar business. Brown has rekindled her friendship with Leonard Lauder and has a future lunch with him on the books, and before you ask, she is not currently interested in selling.
“I know I wasn’t meant for the life I have,” she reflects. “I never felt I was smart. I never felt pretty. I wasn’t a great student. Teachers never thought I would amount to much. My parents never thought I would be a high achiever. They just thought, ‘Oh, she’ll probably be a mother and maybe a teacher.’ Well, guess what? I am both of those things. It’s nice to be in your sixties. There are some days I think I’m pretty, and other days, or many days, that I think I’m smart, but I’m a different kind of smart. I’m comfortable with that now.”
A version of this story appears in the September 2023 issue of ELLE.
ELLE Beauty Director
Kathleen Hou is ELLE”s Beauty Director. Previously, she held the same title at New York Magazine’s The Cut. She’s appeared in publications such as New York, The New York Times Magazine, Vogue India, Forbes, and Allure. She was also a co-founder of Donate Beauty, a grassroots beauty donation project started during the COVID-19 crisis, which donated over 500,000 products to over 30,000 healthcare workers across 500+ hospitals.