“It’s a challenging time,” the longtime Vogue editor in chief said. “I feel we need to be courageous.”
On May 20, at the Cipriani event space across fro m Grand Central Terminal, boldface names from the world of fine art, Hollywood, fashion and politics, as well as the cocoon of philanthropic wealth, gathered to honour the legacy of photographer Gordon Parks. The invitation to this annual gala, which supports the foundation that maintains Parks’ archives and highlights his enduring impact, described the evening as a celebration of “the arts and social justice”. Parks, who died in 2006, used his camera as a weapon to combat racism and prejudice. He regularly turned his lens on the disadvantaged and the overlooked, as well as many of the extraordinary Black men and women of his generation.
In recent years, the honorees have included artists Amy Sherald and Mark Bradford, activists Colin Kaepernick and Myrlie Evers-Williams, and philanthropist Clara Wu Tsai. This year’s celebration turned the spotlight on civil rights veteran and former Ambassador to the United Nations Andrew Young, Bethann Hardison, who has spent decades advocating for Black fashion models and artist Rashid Johnson. The evening also honoured Anna Wintour – a distinction that left the studiously decisive professional somewhat flummoxed.
Wintour is the longtime editor in chief of Vogue and the chief content officer for the publishing behemoth Condé Nast, whose stable of magazines includes Bon Appetit, Teen Vogue and New Yorker. She is the mastermind behind the Met Gala, which lit up the pop culture cosmos last month. In many respects, Wintour, at 75, remains the most recognisable face of the fashion establishment.
But fashion, at the level where Wintour has long served as gatekeeper, and with its subjective assessment of aesthetics, has struggled more than most industries with diversity and inclusivity, from the pages of its magazines to its corporate boardrooms. And despite moments of intense focus on racial justice, big changes have often been superficial and real change has been slow.
Five years ago, during the powerful sweep of the Black Lives Matter movement, editors, designers, stylists and others within the fashion industry were emboldened to confront the powers-that-be with a list of outrages that included pay inequity and assertions that they were actively disrespected in their workplace.
Critics recalled Vogue‘s cover from 2008 that featured LeBron James and Gisele Bündchen, which some felt mimicked a King Kong and Fay Wray movie poster. Junior editors of colour at Condé Nast complained of being asked to police the way Black cultural touchstones were treated in the magazines but not given real authority over stories as they moved from idea to reality. Designers of colour voiced frustration over not being considered for top creative jobs at major brands.
Much of the agitation was aimed at toppling Wintour from her nearly 40-year reign atop Vogue, where she has been more than an editor in chief. She recommends designers for jobs; she ushers models into the big leagues; she has the ear of corporate titans, political leaders and would-be presidents. She raises copious amounts of cash for Democratic candidates. But despite countless progressive influencers and righteous antagonists pressing their full weight against her years of deeply rooted influence, Wintour stood firm. Apologetic for her failures and blind spots. But determined.
“I felt I had let people down,” she said. “Honestly, I’m someone that believes if I’m at fault, you can’t hide. You have to go out and learn and try to do something about it.”
She committed to make change. To broaden the creative voices in Vogue. To widen the pipeline to the most desirable and competitive jobs in fashion. To open her eyes and to listen.
And she made a promise: “I recognise that there are moments and times people within the company, without the company, when they haven’t felt as welcome as they should be,” Wintour told The Washington Post in 2020. “And I would just say to all of them that we are working as hard and as fast as we possibly can to change that perception and to change it also as a reality.”
“I will take full responsibility if the next time you and I speak, there isn’t a sense that change has come or is being accomplished, or at least it is moving forward.”
Since then, Condé Nast established a mentoring programme for current employees and maintains paid internships to help ease the financial burden of aspiring ones. Wintour is leaning into Photo Vogue, an initiative started many years ago in Italy that consists of exhibitions and a database to which photographers can submit their work for assessment and, possibly, a job. In January 2021, the magazine published its first cover styled by a Black woman, Gabriella Karefa-Johnson.
And, of course, there was the recent Met Gala overseen by Wintour, the one celebrating Black style, perhaps the most public manifestation of change. The one that was accompanied by four different Vogue covers featuring four different Black men: Colman Domingo, A$AP Rocky, Pharrell Williams and Lewis Hamilton, as well as a video that oozed Black brotherhood and sisterhood. It was the gala that opened with 20 Black men in white tie singing Motown – a choir that brought the Black church, Black music and Black history to fashion’s biggest night. It was a gala featuring a blue carpet where, to quote a droll Domingo, Black men “put that shit on,” which is a colloquial way of saying that they had tremendous style, and it was surely appreciated.
But accepting an award from the Gordon Parks Foundation?
“I was hesitant, I’ll be honest,” Wintour said. “I mean, I felt like, is this deserved?”
On a chilly and rainy morning in April, at the employee entrance to the Metropolitan Museum of Art, an unglamorous street-level doorway around the corner from the grand staircase upon which famous guests would later promenade into the Met gala, a Vogue assistant hustled in with two shopping bags containing a selection of floral arrangements in delicate pastels. They were meant to gussy up the earth-toned library in the Anna Wintour Costume Centre in advance of its namesake’s arrival.
Wintour had agreed to continue the conversation of five years ago, to discuss diversity, equity and inclusion and assess how much progress had come after the racial justice uprisings sparked by George Floyd’s 2020 murder. She would lament the calls from the White House to eradicate all references to diversity. And she would consider her own professional legacy.
She walked in clutching a Starbucks cup, wearing a dark leather coat and strands of gemstones around her neck, her signature bob nothing but perfection and her ubiquitous sunglasses nowhere in sight. She greeted everyone warmly and, during an interlude of chitchat between more formal questions, admitted to a special delight in the fact that Colman Domingo would be presenting her with the award from the Gordon Parks Foundation. “Did you see Sing Sing? ” she asked. “I loved it.”
In a chat about fashion as identity, the importance of diversity in the current political climate and her personal – and very public – learning curve, Wintour is not one to latch on to the other person’s gaze. Her eyes drift downward and away. But she repeats her conversation partner’s name, a gesture that is both intimate and authoritative. She speaks quietly but firmly on subjects some would like to see excised from polite conversation because they can be difficult.
Like a lot of companies, Condé Nast had pledged its allegiance to reframing its workplace structure to promote fair treatment of those historically undervalued. In the years since, however, companies have gone from filling their social media feeds with black squares to indicate their solidarity with the Black Lives Matter movement to wiping all references to diversity, equity and inclusion from their websites and their corporate ecosystem. Condé Nast struggled, too. In 2021, it fumbled the hiring of Alexi McCammond as editor in chief at Teen Vogue, arguably the company’s most self-consciously inclusive brand, when her past racist tweets ignited a fury with the staff and online. Its chief diversity and inclusivity officer left in 2024 as employees wrestled with divergent responses to the war in Gaza.
But the company has hired a new diversity and inclusivity officer who is tasked with helping Condé Nast better reflect the world in which it exists through its hiring, retention and promotions. It continues to publicly document its progress toward full representation. While the Trump administration aims to halt all diversity programmes, weed out “woke” sympathisers from the nooks and crannies of every industry and muzzle conversations about racism and inequity, Condé Nast, unlike Meta and Google, continues to make a public effort. Wintour presses on. And in 2025, that alone is something of a win.
“We have certainly tried to make progress. We’ve tried to make it feel a more welcoming environment to everybody,” Wintour said. “I do diversity and inclusivity meetings with the Vogue teams every several weeks. A different person runs it every week, and they ask me questions or I ask them questions. And it’s a forum that is completely off-the-record where they can ask me anything, and they do.”
“They bring up questions around content and make suggestions in that forum about pieces, content we should be thinking about. So that’s very helpful to me,” she continued. “I’m also sensitive to the fact that it’s me. I hope they feel that it’s an open forum, but maybe they’re a little bit more careful than if it was just a group in the room. But I do think it’s an honest exchange of ideas.”
“I don’t want to say that we don’t have more work to do,” Wintour said. “I think there’s always more work to do.” That work can also be messy and fraught and no matter how much is done, it’s never really enough. Wintour sometimes steers clear of specifics as if they are verbal landmines.
As a matter of pure numbers, the publishing giant’s diversity statistics have ticked up and down. Senior leadership in 2020 was 5% Black (77% White). In 2023, it was 6% Black (75% White). In 2020, new hires were 13% Black (52% White). In 2023, that number was 9% Black (50% White). But anecdotally, there has been evidence of a shift. In 2024, for example, the magazine published a story about a Darfuri activist working to raise awareness about the ongoing violence in Sudan.
“I do think that the magazine’s scope has become more inclusive,” said writer Alexis Okeowo in an email. “I couldn’t, and still can’t, get any other outlet to publish long-form coverage of the ongoing massacres and sexual violence there, but Vogue immediately took my pitch.”
“My editor told me he had been hoping for a story on it.”
In recent years, Wintour has leaned on a kitchen cabinet of women of colour for advice, women who represent a broad swath of the culture, not simply fashion or publishing. She declines to name them out of respect for their privacy – and perhaps because in 2025 no good deed goes unpunished on social media. She has learned from the editors of the more than two dozen global iterations of Vogue that differentiating between diversity and inclusivity is a complex and nuanced undertaking.
“It’s interesting to hear from India or Japan and what is important in those countries. That I think teaches [you] a lot about inclusivity and listening and being diverse at the same time,” Wintour said. The exact distinction between diversity and inclusivity is “not clear to me. I think it depends on what country you’re in and what their cultures are and you have to always be listening to the people who are there on the ground because it’s not like one thing. It’s so many different opinions and different cultures weaving together.”
She has tried to broaden her cultural diet, which has included films such as Tyler Perry’s The Six Triple Eight and, of course, Sing Sing. And the experience of this year’s Met Gala, with putting together the May issue, meant working with more Black models, stylists and photographers – some of whom had never worked for Vogue and others, such as stylist Law Roach, who had not done so in such an immersive way.
“I listened a lot to Colman and Pharrell,” Wintour said. “Each one of our co-chairs and [writer] Jeremy [O. Harris] and all the people that we’ve talked to along the way have talked about how fashion gives them, and how they dress gives them, a sense of clarity and identity [and] self-respect in how they present themselves to the world. And I think that’s something that is often not sufficiently appreciated.”
The Met Gala raised the profile of designers who were included in the exhibition as well as those who dressed guests and those who, for the first time, hosted tables. But some also approached the project with considerable scepticism, or at least, caution. Blackness, after all, is complicated. And Black style deserves more than lip service or a single night of celebration.
“As a Black designer, it’s a little bit more than a theme. It’s beyond that. It’s a decision that we have to make every morning just to move throughout society,” said Jerry Lorenzo. “In the beginning, I’m not sure how and if I fit into it.”
Most people have probably passed someone on the street wearing Lorenzo‘s Essentials line of sweatshirts and trackpants in dense cotton. But his main collection for Fear of God is something else entirely. It’s loose-limbed, tailored elegance in earthy tones and luxurious fabrics. Minimalist in cut and sultry in sensibility, it speaks quietly but confidently. While Lorenzo had attended the gala before, this was the first time he had the wherewithal to consider hosting a table. The decision to do so came after significant thought about the way in which Black style would be highlighted at Wintour’s event.
He likened some of his concern to tokenism and the oversimplification of a complex history. “I remember growing up in, and this may be a really bad reference, but just growing up in an all-White school system. Black History Month [comes], and you’re expected to be the Black historian. It’s a very similar feeling. You’re expected to be an expert of a subject that is so multifaceted. It’s so deep. It’s so entrenched. And it’s so heavily weighted, in so many different areas; it’s not a monolithic theme.”
“Obviously, I found my peace in it, and I found my responsibility in it. I found my joy in it and my happiness,” he continued. “But anytime you’re expected to [be] one of the many voices that speaks and represent for us as people, it’s a heavy responsibility.”
He assembled a guest list of artists and activists including Sherald, Ryan Coogler, Yara Shahidi, Andre Walker and Arthur Jafa. His work made a statement on the blue carpet about the breadth of Black style. It can be flamboyant and boisterous. But it can also simmer in hues of black, chocolate, charcoal and grey.
“If my kids are unable to be educated on our influence in this country, whatever little platform I’ve got, I’ve got to be able to say, ‘Hey, this is us. This is the history of us,’” Lorenzo said. “I do believe that there is divine timing in all things. And so it’s my responsibility to stay in line so that when these moments happen we don’t have to get ready. We’re just ready to walk in.”
The timing of the gala was both a rebuke to those who treat diversity like a flaw that must be hidden and an opportunity for Wintour to loudly champion it with the full weight of some parts of the establishment behind her. Vice-President Kamala Harris attended the gala dressed by Off-White. But there were no equally high-profile Trump Republicans.
“Change happens over time. I feel like there are little steps to change, and I feel the people that have the power are now hyperaware of the sort of discrimination that happens. I do feel like it’s still tokenism in a way, but it’s still changing,” said designer Fe (pronounced Fee) Noel, who attended the gala and dressed makeup artist Pat McGrath. “Someone like Anna, for instance, she sees; she knows; she understands. Anna can only do what’s in her power to do. Like what she can do at Condé Nast and who she puts in the magazines and who she highlights and profiles and all of that stuff. And there’s always going to be backlash. There’s some people that might still say, this is not enough.”
“We can’t measure it like that,” said Noel, whose work is influenced by her Grenadian heritage. “This is a start. This is a good start.”
The question, of course, is what part can Wintour play in making sure that the gala was not a one-off, that it was not akin to a Black History Month celebration or a bunch of black squares on Instagram? All those Black designers who had such a significant presence on the blue carpet and in the exhibition are, after all, at work every day.
“It has to be a continuing conversation. And their presence, the presence of so many talented designers of colour, we need that representation,” Wintour said in a conversation after the gala. “We need that representation not because only it’s the right thing to do. It’s because they’re so goddamn good. They’re just brilliant. And I felt that showed.”
The first Black man to shoot a cover for Vogue was Tyler Mitchell in 2018. Mitchell went on to photograph Vice-President Harris in 2021 and to shoot A$AP Rocky for the May 2025 issue celebrating Black style.
But Gordon Parks was the first Black photographer at Vogue. He shot fashion for the magazine as early as the 1940s. His heyday there was in the thick of the 1960s when the rigours of the previous decades were giving way to the baby boomer youthquake. But fashion and style were both woven throughout his work, in the way that he captured the quiet self-regard that Black people maintained throughout segregation or the ways in which clothing could be a contemplative lament in the images of working class folks like Ella Watson in his American Gothic.
A concern for self-presentation was also reflected in the way in which he moved through the world, wearing his leather bombers, silk scarves, cowboy hats and camel jackets. Parks was a bit of a dandy.
His fashion photography captured the looks of the moment and the mere fact that it was he who made the pictures, that it was the gaze of a singular Black man that was helping to define elegance or cool was significant.
“There is something incredible about his access to this world of fashion in those early years as a Black man. It really hasn’t been unpacked fully, I don’t think,” said Rebecca Tuite, a fashion historian working with the Gordon Parks Foundation. “It is incredibly unique. He’s the only Black man doing that at that time. And it’s a level of access that’s huge.”
Parks also photographed fashion for Sports Illustrated as well as Life magazine, where his work was featured on the cover. But at Vogue, which held a particular magic for him, he never photographed a cover, Tuite said. And so, in some ways, the award to Wintour is a way of acknowledging the role that fashion played in Parks’ career, in making note of what could have been and what actually was.
“Gordon was the first Black photographer at Vogue but he never had a cover. It was a big deal about Tyler Mitchell, but to be honest, that should have been Gordon,” said Peter W. Kunhardt, Jr. executive director of the Foundation. When inviting Wintour to accept the award, “I said, ‘Do this for Gordon. Make this about celebrating the legacy of Gordon Parks and what Vogue did for him.’”
“My biggest concern is that everybody will be there to celebrate her, and I don’t want her to undermine it by saying, ‘I don’t understand what I’ve done.’ That’s undervaluing it,” Kunhardt said. “What she’s doing with Vogue is admirable. What she’s doing is leading it into the future.”
Wintour assumed the top job at Vogue in 1988. She has described the position as her dream job. That has not changed, she said, even though the times have. And so when she accepts an award celebrating the arts and social justice, she will do so thinking about the Costume Institute exhibition the gala celebrated, the excitement that surrounded it and the heartfelt notes of thanks she received afterward. She will also consider Parks’ legacy and how it might connect to Mitchell, who exudes such confidence and clarity of vision, and other young Black photographers who might want to shoot for Vogue. She hopes to be wearing an ensemble created by a standout designer of colour – the gods and express delivery willing.
She will also be thinking about the need for truth and facts. How can she shine a light where she failed to do so before? How do you answer the doubters with actions? How do you respond to the moment?
“I think it makes one feel that one’s work is even more important and how can you best use your work, within the confines of what we do, to tell the truth and to stand up for the values that I know we all believe in,” Wintour said. “It’s a challenging time. I feel we need to be courageous.”