As the legendary Vogue editor searches for a new head of editorial content, we’re analyzing the influence of Anna Wintour’s first Vogue cover.
Whispers of Anna Wintour stepping down from Vogue have permeated the fashion stratosphere for years. On a quiet Thursday in June, 2025 the legendary editor confirmed she is searching for a new head of editorial content. Though Wintour has stepped down as editor-in-chief, she will remain as Vogue’s global editorial director and Condé Nast’s global chief content officer.
Vogue has come a long way since its beginnings as a weekly newspaper when it was founded in 1892. Prior to Wintour joining the magazine, Diana Vreeland was one of the most influential editors who shook things up from 1963 – 1971. Grace Mirabella ushered in an era of safeness and conservatism when she took over from 1971 – 1988. Next came Anna Wintour.
Anna Wintour’s first Vogue cover was groundbreaking for several reasons:
The high low fashion concept
High low styling existed long before Wintour, but many credit her November 1988 Vogue cover as revolutionary for this simple fact. Years before Carrie Bradshaw wore a tutu and sheer white bodysuit–decades prior to thrifting becoming mainstream–Anna Wintour broke the fourth fall of fashion with her an outfit combination that was reportedly so not-the-norm, it caused the printer to call up Vogue and ask if it was a mistake.
Model Michaela Bercu, photographed by Peter Lindbergh and styled by Carlyne Cerf de Dudzeele, wears a haute couture Christian Lacroix bejeweled cross sweater with a pair of stonewashed Guess jeans. The baroque fantasy of a sweater was originally part of a suit, but the skirt didn’t fit. And so, the outfit was thrust into an entirely new vein of styling unfamiliar to Vogue at the time; one that that took inspiration from personal style and how real life stylish women wore their clothes. It was fun. In today’s media landscape dictated by brand credits and full look policies, it would be amazing to see this kind of cover styling make a comeback.
“What none of us expected was to run that picture on the cover, least of all the magazine’s printers, who called up and asked with some consternation, ‘Has there been a mistake?'” wrote Wintour in 2012. “I couldn’t blame them. It was so unlike the studied and elegant close-ups that were typical of Vogue’s covers back then, with tons of makeup and major jewelry.”
The smile
The former traditional reserved poses, serious gazes and unapproachable looks were thrown out the window with this cover too. In fact, Michaela Bercu is smiling, her hair windswept and her eyes slightly closed, looking off in the distance. It almost looks like it could be a street style photograph taken by one of the many permanent fixtures of street style photography today.
It’s interesting that Wintour has become so well-known for wearing her dark sunglasses over the years, but much like the smile and distant gaze on the cover, expression is everything, and in the best cases of art, like the Mona Lisa, left up to one’s own interpretation. Most of all, maybe readers could see a little bit of themselves in Bercu’s easygoing, everyday gaze. Bercu looks young and not-so-serious, a throwback to former Vogue editor-in-chief Diana Vreeland’s sentiment. Vreeland has been credited with revolutionizing the fashion magazine industry with youthful culture and creating the term “Youthquake”.
Removing the studio
Most prior Vogue covers were shot by studio photographers like Richard Avedon, with models posed against flat backgrounds. Grace Mirabella, Wintour’s predecessor, often showcased models with closely-cropped portrait imagery, zoomed in on the face without showing much outfit detail. Makeup was heavy and a major focus. Jewelry was elemental to the details, with earrings and necklaces often heavily showcased. For Anna Wintour’s first Vogue cover, she deconstructed the concept by removing jewelry, replacing the studio setting with one that mirrored real life city streets that strike the viewer as familiar and real. She challenged the beauty look with something barely-there.
The year was 1988. It was relatively early in German photographer Peter Lindbergh’s career. And in some ways, this cover stood as the beginning of a whole new era of model photography–one that showcased a sort of raw realness that was also untouchable. Maybe it was the kind of imagery that turned models into supermodels. After all, in 1989, Lindbergh photographed then-little-known Linda Evangelista, Naomi Campbell, Tatjana Patitz, Cindy Crawford, and Christy Turlington together for the January 1990 British Vogue cover, which put them on the map as new kinds of celebrities.
The whimsical cover lines
“Paris couture: haut but not haughty,” read the most-remembered cover line from Wintour’s first ever Vogue cover. It was fun, witty and approachable and a departure from her predecessor Grace Mirabella’s cover lines, which often were often more direct and with a service angle relating to makeup, hair, health, or seasonal style transitions.
Previous Vogue editor Diana Vreeland had a way with words and witty sayings, writing things like “A little bad taste is like a nice splash of paprika,” for her “Why Don’t You” column for Harper’s Bazaar prior to joining Vogue. Today, a good, cheeky cover line is almost as essential to the print magazine business as the imagery behind it all.
The Vogue cover of today
There are so many ways to interpret Anna Wintour’s first Vogue cover. Could the cross be representational of rebirth? Was the entire point of it to democratize fashion in the high-fashion media space with one affordable item–the Guess jeans? At the end of the day, Wintour has said in her own words that it simply came down to her love of the image. “I had just looked at that picture and sensed the winds of change,” she wrote. “And you can’t ask for more from a cover image than that.”
In her 37-year career at Vogue, she didn’t just change Vogue. She has been credited to changing the entire media and fashion industry. One of the biggest shifts? The celebrity magazine cover, which really became incredibly normalized in the early 2000s. Today, it’s normal for every single major magazine cover to be dripping with an A-list celeb, but it wasn’t always like that. Prior to Wintour’s reign, it was mostly models on the cover, save for a few occasional reserved A-list actresses who also dabbled in fashion and modeling, like Audrey Hepburn, Sophia Loren, Jane Fonda or Grace Kelly.
For Vogue’s May 1989 cover, Wintour cast Madonna, photographed by Patrick Demarchelier, wet hair, red lipstick in all. She emerges from a bright blue pool, smiling with a white bathing suit strap visible. Celebrities of the moment would later become the norm on fashion magazine covers.
The story behind Wintour casting her first ever celebrity cover is also so interesting. Wintour was chatting with a man she’d never met on a plane, and he asked her what she did. When she told him, he said, “I love Vogue. It makes me think of Audrey Hepburn, Grace Kelly, and I think about all these amazing icons. Of course, Vogue could never be Madonna.” In an interview, Wintour said, “That was like a lightbulb going off, because I thought Vogue should be Madonna.”
The shift represented several things: a new generation of fashion media, dipping a toe into provocation and the ultimate influence of pop culture on fashion and vice versa.
Images// Vogue
Leave a Comment