Tory Burch and I go way back. Her Reva ballet flats, with the brand’s T logo emblazoned on a medallion affixed to the toe, were a status signifier at my high school, an assignation of class in the mid-aughts. Then, they were everywhere. Five years later, she made an appearance on the fashion show of the moment, Gossip Girl, alongside star Blake Lively, who seemed the perfect avatar for the brand: blond, magnetic, a little preppy, a little boho, the consummate New York Upper East Sider. It was an aesthetic of which Burch herself, who lived at the Pierre Hotel and was a fixture on the benefit circuit, was the perfect embodiment. The look was so Tory, a wardrobe made up of Moroccan-inspired tunics paired with crisp white trousers, graphic-print shift dresses, and shorts worn with sweaters layered over collared shirts.

Burch found success almost instantly, as well as the sort of misogynistic undermining that so often confronts women who achieve it. A 2004 New York Times profile touting her new brand was laced with snark and condescension. (The journalist, who was male, described her as a “delicate blonde” and referred to her speaking with a “baked Alaska tone.” )

So it’s especially gratifying that 20 years later, Burch has built one of the biggest and most robust sportswear brands in the history of American fashion. Her label has grown exponentially over the past two decades, thanks to both her eye and her entrepreneurial prescience. Burch anticipated the e-commerce boom and launched Tory Burch on the internet rather than through traditional wholesale. She knew how to slowly build the hype with her in-store experiences, starting with a small outpost in the downtown neighborhood of NoLIta that was decorated in orange lacquer and chinoiserie. It was all conceived to exude good (and expensive) taste, but in a way that felt more accessible (and attainable) for people who didn’t actually summer in the Hamptons.

Today, Burch has more than 370 stores worldwide and annual revenue that has been reported to approach $2 billion. Last year, she was nominated by the Council of Fashion Designers of America for American Womenswear Designer of the Year, the industry’s equivalent of an Oscar nod for Best Picture. It’s all a reflection of the fact that we are in the midst of what has been dubbed by armchair experts and social-media folk as the Toryssance. Burch’s vision has shifted from that shiny, country-clubby lifestyle to one that feels more grounded in her own idiosyncratic personal style. Instead of the shifts, there are sci-fi-ish hoop-skirt dresses inspired by deconstructed crinolines. Alix Earle, Chloe Fineman, Uma Thurman, and Jeremy O. Harris sit front row at the shows. This past season, both Emily Ratajkowski and Paloma Elsesser walked her runway. Two decades in, Tory Burch has entered her cool era.

“I didn’t consider myself a designer in the beginning,” Burch tells me. We’re talking in her office in Manhattan’s Flatiron District, a mix of classic and modern that’s done up in light woods and deep blues, with gilded touches throughout. Family photos are on display everywhere; she is the mother of three boys, and two of her three stepdaughters work with her. Burch sits cross-legged on a sunken-in couch that she says is around the same age as her brand. She is wearing ivory parachute pants, a matching zip-up top, thick silver spike earrings, and a pair of high-heeled mules with a square toe. “I was a little embarrassed to call myself a designer back then, but I feel now that I’ve earned that badge,” she says. “I learned how to be a technical designer over time.”

It’s a skill evident in Burch’s collections, which are still filled with plenty of pragmatic pieces for the original Tory Burch loyalists, like the tailored trousers, the throw-on-and-go knits, the button-ups, and, of course, those Reva flats. These wardrobe staples, however, now have their own little tweaks and twists that set them apart and give them a certain weight, like a sleeve sewn together to appear scrunched up or a skirt hem with coils of cascading ribbonlike trim. “I’ve always had an eclectic mind,” Burch says, “and so maybe that’s coming through a little bit more.”

Growing up in Valley Forge, Pennsylvania, Burch was surrounded by beautiful things. Her father, Buddy Robinson, had a dandy, effervescent sense of style that would provide much of the visual language for Burch’s clothes. Her mom, Reva, the muse for those famous flats, was another strong influence, with a closet filled with Valentino, Yves Saint Laurent, and Zoran, a designer Burch would later work for.

Burch herself was a tomboy who didn’t like miniskirts and loved hanging out with her three brothers—one of whom, Robert Isen, now works at Burch’s company as chief legal officer and president of corporate development. But despite her mom’s fashion playground of a wardrobe, Burch preferred thrifting for vintage jeans and tees. “I had an area in our house with all of my clothes, vintage trunks, photographs, love letters—everything that was dear to me—and no one was allowed to go in there,” Reva Robinson recalls. “Tory and I would sneak up, and I would show her all of these beautiful fabrics, which she wasn’t interested in,” she says. “Tory was a tough little girl.”

It was early on in the pandemic that Burch’s impulse to go her own way resurfaced. Even though she was happy with the evolution of her business and passionate about her work with the Tory Burch Foundation, which she launched in 2009 to support female entrepreneurs, she had begun to feel detached from the products she was putting into the world. “Over the years, I feel like things became less of a personal vision,” she says. “That’s why I wanted to pull it in, and I think when you look at the success of things, sometimes you go toward that success instead of reinventing that success and having another success. I felt like I had to reinvent the concept of what would be us today.”

A few weeks later, on the set of a shoot for Burch’s Resort 2025 collection, I get a sense of what that looks like. Hip-hop music—Burch’s favorite genre—plays softly throughout the photography studio inside the company’s sprawling Jersey City office, which houses the creative teams. With a Starbucks cup in hand, Burch sifts through the precisely organized racks, smiling at the sight of a fuzzy hand-knit sequined shawl-collar sweater, a candy-apple-green crystal-studded draped goddess dress, and a pair of baggy cargo pants. “We are evolving past the logo,” Burch says. “We want people to recognize the clothes for the clothes.”

Burch follows every shot closely, adjusting the folds on a dress herself so that they catch the right light or pulling a pant leg up over a deep-red boot so it falls exactly the way she wants it to. Her stepdaughter Pookie Burch, who is the associate creative director of design of Tory Burch, stands nearby, occasionally offering her own perspective or debating certain choices. The respectful push-pull between Pookie and her boss-slash-stepmom is endearing, lively, and indicative of the way Tory works. “I think we all teach each other,” she says. “Pookie and I are generally aligned because we’re both not easy, and we definitely have tension at times, which I think is important. I don’t want yes-people around me.”

Some members of Burch’s team, like VP of Design Research and Styling Som Sikhounmuong, have been with her since the beginning. Others, like stylist Brian Molloy, are newer. Molloy, who also works with the Row, says that in recent years Burch “has created space for herself to experiment and take risks, but she’s always thinking of the woman in the clothes—how she lives her life, how she gets dressed. There is an authenticity and awareness, even in her more conceptual designs.”

Sikhounmuong is quick to point out, too, that the customers are responding to this experimentation in organic ways. “Most of the time, we don’t have people coming to us and asking for a specific thing someone famous wore, but instead the clothes and accessories are selling themselves,” he says. “The customers are like, ‘Oh, what’s this? I want to try it.’ ”

The new phase of Tory Burch was catalyzed in 2019, when Burch turned over the position of CEO of the company to her husband, former LVMH Fashion Group chairman and chief executive officer Pierre-Yves Roussel, so that she could focus more on design. For Burch, it inspired a shift in the way she thought about her brand, as she began to move away from designing around specific narratives that defined a digestible wardrobe and toward envisioning a feeling or aura she wanted to develop for the women who wear her clothes.

“Fashion is about tension,” Roussel tells me. “I love disruption, but it has to be meaningful disruption. I think one of the things that explains the success of Tory Burch is the authenticity of the brand. There’s no fake story. It’s real, including her being able to say, ‘I need to disrupt myself,’ which isn’t easy.”

After working with some of the most prolific creative directors in fashion during his time at LVMH, Roussel understands the difference between an idea with longevity and one that will quickly dissipate with the passing of a moment. “When you look at the creative directors of the brands now, a lot of them are men. There are very few women,” he says. “By nature, when a man designs for a woman, it’s a fantasy. So it’s an intellectual and creative construction,” he continues. “In a way, Tory has gone through that. She had to go through something that became a construction of her. But now, she has taken a distance from that aspect of the brand, and she would say that the brand is even more of a reflection of her … of her creative imagination.”

As much as Burch’s current design ethos is closer to her own sense of style, she always thinks about how she sees other women dressing. “People used to say to me, ‘Why don’t you design how you dress?’ And I thought that was so funny,” she says. “I knew I had this Herculean effort ahead of me. I also knew that we had a pretty big business at the 10-year mark, and I wanted to be careful because I had a ton of employees already. I didn’t want to jeopardize the business. I had a responsibility,” she explains. “That’s the challenge for me. How do I design things that I wouldn’t wear but I want to see other women wearing?”

Burch also wanted to give those women a signature scent, which led to the launch of her new fragrance, which is out this month. It’s called Sublime, a word that was introduced into the Burch world as a print in the Fall 2024 runway collection.

The campaign for Sublime stars Kendall Jenner, and the scent is a mix of rose, vetiver, and leather—a sexy but not overpowering smell that Burch explains is meant to represent “dichotomy, because women are filled with dichotomies.”

What Burch has been able to do is incredibly rare in the fashion business. Although fashion itself is supposed to be about change, the industry can often be risk-averse. But instead of playing it safe or falling back on fantasy, Burch has taken the idea of leaning into personal identity and intuition and turned it into a blockbuster concept—one of which Tory Burch, the brand, but also Tory Burch, the woman, are living proof.

When I ask about what the future holds, Burch straightens up and cracks a curious smile. “I don’t think about where we’ll be in a year. It’s more about continuing a dialogue that we’ve started,” she says. “I love that women today are more individual than they’ve ever been. I don’t feel like there are a lot of rules anymore, and I think that’s a wonderful thing.”