On Leadership Style: Quiet Authority and the Power of Collaboration

Hillary opened with something she has become known for saying: she is an introvert leading one of the loudest brands in the world. Far from being a contradiction, she sees it as an advantage.

"I listen a lot more than I talk, and I think that allows me to see people really clearly and to see things in people they can't see in themselves. I think of myself as a curator of teams, as a conductor. It's not really about me at all."

For Rachel, the approach to leadership was shaped by years of witnessing what she did not want to replicate. Two decades in an industry where authority too often meant intimidation left her with a clear mandate for her own work: build something different.

"Fashion is a very collaborative business. There is no genius. Every creative director is supported by a massive team, internally and externally. I really want people to feel that they are in a space based in collaboration and trust."

At Proenza Schouler, that meant entering an established house with reverence rather than disruption, recognizing that the people already there were experts in their own right, and earning the trust of a team that had not previously been led that way.

On Brand Evolution: What Changes and What Never Does

The question of when a brand should evolve and when it should hold its ground is one both leaders think about daily. Hillary's answer was precise.

"Every great brand has to stand for something, and what the brand stands for, what the brand codes are, they do not change. But is it resonating in today's culture? Is it relevant in today's zeitgeist? That is the question we are always asking."

For Victoria's Secret, the brand codes have always been rooted in sexy, glamorous, accessible luxury. What has changed is the cultural filter. The new chapter, as Hillary described it, is built around invitation rather than prescription: celebrating confidence and sensuality on your own terms, reflecting a global landscape with multiple definitions of beauty, and giving women agency rather than dictating a singular standard.

"There was a time when I very much felt like I was not enough, like I was never a Victoria's Secret customer until I started working at Victoria's Secret. This next chapter is about how do we spark joy, how do we celebrate sexy on your own terms, how do we reflect all kinds of micro-cultures."

Rachel's version of the same tension plays out across two distinct brands. DIOTIMA is deeply personal and explicitly political, rooted in her Jamaican identity and a radical resistance to the flattening of women's narratives. Proenza Schouler is more cerebral, but driven by the same underlying instinct.

"I think what I took issue with, having been in this industry for so long, especially as a black woman, is that narratives are often flattened and simplified. That desire to bring nuance comes through in both brands, but the starting point is quite different."

On the Women's Economy

One of the most striking moments of the conversation came when Hillary reframed Victoria's Secret not as a consumer brand but as a women's economy.

Thirty percent of the brand's cotton comes from female farmers in Alabama. Education programs run across factory partners throughout Southeast Asia. The annual fashion show is the second largest glam day in New York, driven almost entirely by female workers. The board is 80% women. The executive team is 75% women. The workforce is 86% women. Charitable work is focused entirely on women's health, including funding female doctors to conduct breast cancer research.

"It is really a powerful thing, and something that we don't tell people. And so I'm thinking a lot about how to tell that story, because in the consumer's mind we are still attached to the old Victoria's Secret. The new Victoria's Secret is absolutely focused on making women's lives better."

On Public Presence: The Cost of Stepping Outside Yourself

Both leaders spoke with unusual candor about the weight of visibility and the line they have each drawn around it. Rachel was direct about her discomfort with the performance aspects of public life, and equally direct about why she has made peace with it.

"I became a designer not to be in front of a camera or on a runway, but to be behind the scenes, making things with my hands and making people feel incredible. But you can't have one without the other."

What she has resisted is the industry's long-standing obsession with presenting women as pristine and unattainable. Her own answer to it is deliberate visibility around imperfection: the last five years of her life, she said, have been a complete breakdown and rebuilding, and she considers that beautiful.

"Having this ease about complexity, nuance, imperfections, being a little bit crazy, it's nice to see in a public way. I want to see more women embrace the fullness of their being."

Hillary's version of this reckoning came years earlier, at a previous role. She described walking, listening to Martha Beck's book The Way of Integrity, and sobbing when she realized she was being asked to step outside of who she fundamentally was. She left. She took nearly two years off. And she made a decision she said she returns to constantly.

"I made a conscious decision in that moment that I will never be anything other than who I am, one hundred percent. Anything that requires me to be otherwise is just not for me. I am not a CEO who is on a lot of stages. I pick them very carefully. I do them mostly for causes I believe in and people I believe in."

The result, she said, is something she never anticipated: a depth of connection and camaraderie with the people around her that only comes from being fully recognizable as yourself.