50 Unforgettable Images From W Magazine’s Half Century of Style

“This was my first time properly shooting photography with Yorgos Lanthimos. We’re very comfortable with each other, and he let me choose my dogs, and it’s my favorite shoot I’ve ever done. I hope the dogs feel the same way.” —Emma Stone, Actor

“We really wanted this shoot to be just about Naomi Campbell. She is a timeless beauty, and it was great to pull back and let it be all about her.” —Ibrahim Kamara, Stylist

“This picture tells a story about the ’90s: The fashion is Tom Ford’s first collection for Gucci; the models, Amber Valletta and Shalom Harlow, were best friends. This was my first story for W, and the idea was to go on a road trip following in the footsteps of writers like Jack Kerouac and William S. Burroughs, stopping at all their haunts throughout San Francisco. I was reading a lot of beatnik poetry at the time and wanted to capture a free-spirited feeling, a time and a place that we can all draw inspiration from.” —Craig McDean, Photographer

“I love this image because I want to be her.... She would have been going to Studio 54 that evening—my dream!”—Kate Moss, Supermodel

“We were shooting Winona Ryder shortly after her shoplifting charge, and I thought, Could we put her in that free Winona T-shirt? It was so popular. The fashion department was skeptical (it’s a T-shirt!), and the bookings department was skeptical (she will never wear it!), but I said, ‘Let’s ask.’ We called a tiny novelty shop in Los Angeles and had boxes and boxes of the tees shipped, in every possible color and size. In the end, Winona was a dream. She loved the risk of doing something different, and she loved the picture. It’s one of my favorite covers to this day.” —Joe Zee, Fashion Commentator, Journalist, and Producer; Fashion Director at W, 1995–2005

“I remember thinking this picture of Frank Ocean was going to be one of those images that stay with you. It just looked like the perfect reflection of the times.” —Miuccia Prada, Designer

“This was the first time we designed a children’s line, and we loved exploring the kids’ playful energy and creating a collection where their personalities could shine through.” —Ashley Olsen and Mary-Kate Olsen, Designers of The Row

“The combination of Kristen McMenamy and Tim Walker is so powerful; the image is so good...just as much today as it was when I first saw it. Heaven.” —Marc Jacobs, Designer

“What amazes me about this shoot is that it was directed by Denis Villeneuve…whose movie Dune basically inspired my entire spring 2022 couture collection. Anytime you see your work on a cover, it’s a total thrill, and most of the time a total surprise. But this cover, starring Zendaya, the muse of Dune, and thereby the muse of our entire couture collection, felt like some sort of cosmic couture destiny.” —Daniel Roseberry, Artistic Director of Schiaparelli

What was it like working with Bad Bunny? He’s playful, fucking gorgeous, down to be femme, masc, emotional, and goofy. He was up for anything, an utter professional, and cool as shit. The shoot was a dream. It was the Grammys weekend. He won big and wore a sunflower as an accessory. We raged all weekend, hit all the afterparties. No, I’m lying—I wish.

What does W mean to you? I’ve been reading W since I was 5. I would grab it while my parents shopped at Ralphs. I blame W for my expensive taste. —Martine Syms, Artist

What was it like to be posing for W’s cover when you were pregnant for the first time? I felt a little vulnerable. At that time, there were still puritanical ideas about showing a pregnant body. Thank god Rihanna has finally buried that, hopefully forever.

Do you remember how you felt when this issue first hit newsstands? I genuinely was a little embarrassed, given what I just mentioned. There was some dismay about W showing me pregnant on the cover.

How do you feel about this image today? I just love it! I love the photograph and love that I was incubating my little Apple. One of the benefits of being in the public eye, which can be complex, is that so many of my chapters have been documented visually. —Gwyneth Paltrow, Actor and Entrepreneur

“This picture was taken in the backyard of my old house in Houston. Being in W meant the whole world to me at that time! It was the most fabulous magazine, because it didn’t do the same things as all the others. Everyone looked for W, and when this came out, all my friends came up to me and commented on it. I thought, If I can live up to this story, I’ll be happy!” —Lynn Wyatt, Social Legend

“This was a story of a woman who was lonely and living in her own fantasy world. She had no time or date in her looks, or on her mind.” —Mert Alas & Marcus Piggott, Photographers

“It’s all there in one image: so much about what made Karl Karl. There is the humor, of course, and the sense of absurdity that he loved—one of the world’s most elegant designers tucking into a burger at McDonald’s. It also captures his appreciation of high/low. Karl hated anything that was middlebrow, so there he is wearing a black designer suit, probably Yohji Yamamoto, with a custom-made dress shirt from Hilditch & Key, slurping his Diet Coke through a straw.” —William Middleton, Author of Paradise Now: The Extraordinary Life of Karl Lagerfeld, Out in February 2023; Paris Bureau Chief of W & WWD, 1995-1998

“I love this photo and the glamorous ladies I remember seeing in W when I was growing up in the ’80s. They were so dedicated to fashion. It seemed like such a fun time to be hanging out at Maxim’s in Paris in couture gowns after the Battle of Versailles fashion show! Jacqueline de Ribes and Gloria Guinness knew how to do it!”—Sofia Coppola, Filmmaker

“What at first could have seemed like a W mandate ‘to work with all female photographers’ was, in fact, a liberating, out-of-the-box release. And how easy it was to assemble. There were scores of names: Shirin Neshat, Cass Bird, Sam Taylor-Johnson, Alex Prager, Rineke Dijkstra, Jackie Nickerson, Viviane Sassen, Sharna Osborne, and Dominique Issermann were just the towering tip of the iceberg. The ideas were crazy good and a joy to be part of.” —Cate Blanchett, Actor; Guest editor of the 2018 issue “The Female Gaze”

“I remember not knowing what the picture would look like in the magazine, but I ended up really liking it. I really enjoyed working with Mert & Marcus, and they definitely captured a specific moment in time and in my life.” —Pharrell Williams, Musician

“Creating a work for the cover of W was a terrific opportunity. It allowed for a visual consideration of pictures, words, the body, gender, narcissism, and voyeurism that I knew would reach a large audience. That made sense, because in this time of digital virality, the reach of social media, streaming, and even old-school TV is so massive. And Kim Kardashian and her family, along with billions of other ‘influencers,’ totally rule in terms of visibility and revenue streams.” —Barbara Kruger, Artist

“This picture was taken when we were celebrating Proenza Schouler’s 10 years in business. In it are women who, to this day, we still consider some of our best friends: [back, from left] Olympia Scarry, Victoria Traina, Chloë Sevigny, Lauren Santo Domingo, Jen Brill, Julia Nobis, Vanessa Traina; [front, seated] Meghan Collison, Liya Kebede. Each and every one of them represents an element of the brand. They inspired us then, and they still do, almost 10 years later.” —Jack McCollough and Lazaro Hernandez, Designers and Cofounders of Proenza Schouler

“Begun early during W’s broadsheet days, the In & Out franchise was by turns loved, loathed, and feared. The list covered everything—people, places, politics, food, ideologies—with selections ranging from reasoned to random to silly: Barcelona, yay; the Côte d’Azur, nay. Pasta, out; fennel, ditto. W relished declaring items out at the height of their popularity, be they Nouvelle Society’s big sleeves and ruffles or the cropped pants of the downtown set. In 1989, ‘wearing cheap clothes with expensive ones’ was in, presaging fashion’s ongoing fascination with high/low. Yet people were the core of In & Out. The 1988 edition proclaimed that ‘Michael Jackson and the whole Jackson family, except Janet’ were out. Donald Trump? Most definitely out. Like all long-running editorial features, this one eventually ran its course. But even at the height of In & Out’s popularity, W was nothing if not self-aware. ‘Remember,’ the magazine admonished in 1988, ‘it’s out to take this list as gospel.’ ” —Bridget Foley, Fashion Journalist; Writer and Executive Editor at W, 1989–2010

“The inspiration for this shoot was the artist Chris Ofili’s ‘Afronude’ series. I was drawn to the seductive yet completely pure nature of those paintings: Black bodies as symbols of nature without being objectified or sexualized. I have a hunger for a visual language that presents Blackness in a heightened state, a self-actualized state, a supernatural state of being. That is what comes through in these images.” —Cyndia Harvey, Hairstylist

“This series was shot in two major art cities: New York and Paris. You could say that it was us curating a group show of our favorite artists by photographing Raquel Zimmermann and Freja Beha as an eccentric duo visiting museums and galleries, while clearly featuring the artwork in each shot.” —Inez & Vinoodh, Photographers

“This portrait of the model Guinevere van Seenus is from the first shoot I collaborated on with photographers Mert Alas & Marcus Piggott. It is an image that illustrates a special time for me: It was inspired and encouraged by the talented creative director Dennis Freedman, who helped transplant me from London to New York in 1995.” —Alex White, Stylist; Editor at W, 1994–2011

What is it about this image that resonates with you? It’s a reminder that Lee Radziwill could literally make anything look chic and elegant. There was a simplicity to the way she dressed, but it was never boring—she always looked like herself. She exuded confidence and was never flashy.

When do you remember first becoming aware of her as a style icon? I have always admired Lee, and my fall 2018 collection was inspired by her extraordinary style and her book Happy Times. We were introduced by a mutual friend about 15 years ago, and I instantly loved her remarkably quick wit—she was the queen of one-liners. —Tory Burch, Designer

“Raquel [Zimmermann] was fearless in front of the camera.” —David Sims, Photographer

Tell us about the inspiration behind this image. Did you have any particular visual references in mind? The concept was twins, and so we went full Diane Arbus!

What memories stand out to you from the shoot itself? The beauty of the California desert, the pleasure of working with the wonderful Adwoa [Aboah] and Rianne [Van Rompaey]. The wind was a serious thing. Still, a fashion shoot is more efficient and relaxed than a movie! —Luca Guadagnino, Director

“Shooting my first cover with Kate Moss was a dream come true. I remember it was very organic. We were not thinking about fashion, just about Kate and how beautiful she was. I thought the best way to convey her beauty was to photograph her nude and with hardly any makeup. I just let her be her and move in ways that she felt comfortable. She will always be one of my favorite models to photograph!” —Michael Thompson, Photographer

Do you remember how you felt when you first saw this photo in W? I was so excited to see something that celebrated a return to glamour and strength and unabashed luxury. It was the opposite of the sad, dour moment in fashion that was so prevalent in the ’90s and that I was never a big fan of.

Christy Turlington Burns has been a fixture in many of your runway shows through the years. I was knocked out by Christy the first time I met her, back in the ’80s, when she was a teenager. She’s a true chameleon who can go from playful to elegant, from sexy to strong, but she always shines through, which to me is the essence of a real star. Besides being such a remarkable beauty, she’s a wonderful human being full of compassion, kindness, and humor. —Michael Kors, Designer

“Steven Meisel had the brilliant idea of creating a series of fake campaigns, like this one for a lingerie line that we called Tantrum. The best part was that we interspersed the images with actual ads in the magazine, without any explanation. It took a second for readers to figure out that this was an artistic project and not advertisements for a series of strange new brands that they had never seen before!” —Edward Enninful, Editor in Chief of British Vogue; Creative and fashion director at W, 2011–2017

“This was my first shoot with Emma Stone. We felt like we were on a movie set for some historical empire film, so it was easy to get into character. It was the beginning of a genuine and creative friendship.” —Nicolas Ghesquière, Artistic Director, Women’s Collection at Louis Vuitton

“Not only did each makeup change for this shoot take a minimum of two hours, but the spectacular ‘eye armor’ that Rihanna wore on the cover took my team and me six weeks to custom-make. It was truly a couture process—trial and error, fittings, experimentations. It’s always a pleasure working with Edward Enninful; seeing our mutual vision come to life in such a spectacular manner was a total joy.” —Pat McGrath, Makeup Artist, Founder of Pat McGrath Labs

What do you remember about the planning process for this shoot, based on the idea of “fashion cults”? The sheer scale! I think we had more than 80 trunks of clothes and 39 models. We were trying to highlight the best collections from the fall 2016 season. It was Hedi Slimane’s ’80s-inspired farewell show at Saint Laurent, Alessandro Michele’s ethereal spirit at Gucci, and Prada’s ’50s-inspired brocade dresses. The idea that each designer had their own cult following gave rise to this shoot.

What is it about this story that still resonates today, in your eyes? Surprisingly enough, I think this was a year before The Handmaid’s Tale series came out. I think this image certainly speaks to the chaos of our current times—screaming in scarlet, wanting to be heard! —Rickie De Sole, Women’s Fashion and Editorial Director at Nordstrom; Fashion Editor at W, 2015–2019

“I became aware of W in the ’90s, after I graduated from Central Saint Martins, in London. I’ve got a particular fondness for this image, as I consulted on this Gucci collection, which was my first big fashion break. And at the time, I was working with Gisele a lot, so this makes me pretty nostalgic.” —Katie Grand, Stylist; Editor in Chief and Creative Director of Perfect Magazine

“Brad Pitt called me while he was shooting Fight Club and said he wanted to do a story with the clothes from the film because they were so great. So I read the book, by Chuck Palahniuk, and then invented my own version of the story using the wardrobe. Brad was just wrapping the movie when we collaborated on this. He was in peak shape and in character—to make his character feel more real, he even chipped his front tooth!” —Steven Klein, Photographer

“I remember the feeling of standing among accomplished women, thinking, It’s not about what you wear, your age, or how you look; it’s an attitude. It’s about how you embrace your strength as a woman and build on it, make it glow from within, and share it with the world. Women now are supporting one another more and more, to be united and claim what is theirs. A lot has been done, but there’s a lot more work for us to do.” —Donatella Versace, Designer

“I always associate W with a certain type of exoticism—when I was young, growing up in England, it suggested an idea of New York and America to me that felt fascinating and seductive. This image feels minimal yet lush at the same time—I guess that’s what I seek in my own work now, and in part, that aspiration is due to my early encounters with W, trundling home from school, trying to work out what this thing was that I was looking at!” —Max Pearmain, Stylist

“One of the first things we did when I joined Loewe was relocate our offices to an apartment block in Paris’s 6th arrondissement. This picture was taken just before our debut men’s presentation in that space, before it was even finished—it was still a construction site. This was the first time I’d been shot by Willy Vanderperre, and I remember he very kindly sent me a print of one of the portraits he’d done that day. It was an exciting time, and it was just amazing to have worked with him in that moment, when everything was new and just beginning.” —Jonathan Anderson, Designer

“I had just signed a deal to create Tom Ford Beauty, so this was a beauty shoot. Polishing one’s skin and exfoliating is always important. Of course, this young man already had terrific skin, and this particular part of him had no sun damage.” —Tom Ford, Designer

“W always celebrated people who loved fashion, but a cardinal sin was trying too hard—or appearing to. Hence the annual roundup of Fashion Victims. A dreaded mention on the list was an occupational hazard for even the most admired style icons, including Princess Caroline of Monaco and, here, Princess Diana. Maybe if Diana hadn’t meticulously matched her lipstick and blush to her pink flying saucer chapeau and candy-striped triple bowtie, she would have avoided her ignominious turn as a FV cover girl.” —Christopher Bagley, Writer and Photographer; Editor at W, 1997–2010

“My first magazine internship was at W in the ’90s, and it changed my life. I grew up in El Paso, Texas, the child of immigrants, and the only fashion my mom exposed me to was royalty in Hola! I particularly loved this story because Guinevere [van Seenus] has always had this quiet beauty—never too skinny and always cool and edgy. Craig McDean shot her at Niagara Falls, and a few months after this story came out, in 2004, the tsunami hit Thailand, and Craig donated a print from it for a charity raising money for the survivors. I bought it—and have had one of my favorite fashion moments at home ever since.” —Karla Martinez de Salas, Head of Editorial Content, Vogue Mexico & Latin America; Fashion Market and Accessories Director at W, 2010–2015

“This was from a really fun story photographed by Inez & Vinoodh. We were reimagining the ’70s through a cast of characters, so there was naturally a little disco sleaze going on. At Inez’s suggestion, we gave the model Eniko Mihalik a sort of rich male lounge lizard vibe. Perhaps she was a gay gigolo. I was thinking of Egon von Furstenberg, so I painted on quite a detailed mustache and did some pretty theatrical brow and contouring work. Eniko/Egon came to life in W, and you couldn’t put the gigolo genie back in the bottle!” —Dick Page, Makeup Artist

“It took some doing to land an interview with the Duchess of Alba. She was, after all, the most titled woman in the world. Communications to and from her Madrid palace were conducted by mail. Following a monthslong correspondence with her secretary, a letter on light blue stationery stamped with the Alba crest appeared on my desk one morning. ‘I will be delighted to maintain an interview with the W magazine,’ wrote the Duchess herself; she specified a date four months hence on which I was to appear at Palacio de Liria, her residence, at 10 a.m. On the appointed day, I rose early, as did photographer Simon Watson. We set off with plenty of time to spare—until traffic screeched to a halt, thanks to King Juan Carlos’s motorcade. When we finally made it to Palacio de Liria, the secretary was outside, pacing furiously. “Tarde, tarde!” she berated us. We were hurried through countless rooms—a blur of Goya, Velázquez, El Greco—until we reached a dimly lit salon. When she materialized, La Duquesa resembled an apparition, with her wild mane and a face contorted by copious plastic surgery. ‘I am as I am,’ she said regally.” —James Reginato, Author and Writer at Large for Vanity Fair; Features Editor and Director at W, 1991–2009

“We were in Xilitla

In Mexico

In the gardens of the surrealist Edward James

Shooting a dreamscape

This moment of reverie

My eyes closed in the sun on the roof

Surrounded by flowers and hands in hands, birds singing, bees buzzing, captures that transport

It’s a picture of pure happiness

And I can still taste that glow when I look at it, that joy, that fantasy, that gratitude.” —Tilda Swinton, Actor

“Walter Pfeiffer took this photograph of a shelf in my home filled with photos and things I love—friends and heroes combined! It was my first time working with him, and I was so happy to meet such a great guy in real life. It was a moment of change: I was leaving Vuitton after seven years and starting at Dior...the seven-year cycle!” —Kim Jones, Artistic Director, Dior Men

“As we planned our 2021 Originals Issue, everyone on W’s staff was in perfect agreement that there was no one who embodied the theme better than the legendary Dolly Parton. She has been photographed countless times, so we knew someone unexpected had to shoot her for us. When I first spoke to the director and artist Harmony Korine, he told me he had grown up in Nashville and had always worshipped her. I knew it was a match made in heaven.” —Sara Moonves, Editor in Chief of W

“In 1978, I decided to have this great celebration for Valentino’s 46th birthday at Studio 54, in New York. I asked the illustrator Joe Eula to help me organize the party with a circus theme—and with his usual enthusiasm, he said yes. I was sure that everything would be perfect, but, alas, upon arriving in New York, I realized that Joe hadn’t done anything. He had only three little drawings, with three clowns! I was desperate, so I called Steve Rubell—there were two days to go before the birthday. Steve created a real circus inside Studio 54 with horses, clowns...it was an amazing transformation. And all of New York arrived wearing the most incredible costumes. It was an extraordinary evening and one that is always in my heart and Valentino’s. This picture was taken in Valentino’s apartment, right before we headed to the party.” —Giancarlo Giammetti, Partner at and Cofounder of Valentino

“I like photos that hold memories and emotions. My daughter, Rachele, and I have always been in close dialogue and had very constructive discussions. Having her by my side allows me to keep in touch with what young women think, desire, and struggle with. This picture speaks volumes about our symbiotic relationship, our differences, complicity, and mutual respect.” —Maria Grazia Chiuri, Creative Director of Dior

“I usually take photographs in complete silence, but Lana [Del Rey] wanted to have a bit of music. So she put some country music on her phone, and then I put it in my pocket—so I had this funny sound coming out of my pocket the whole time. She completely let go, and we had such a great shoot because of it. She was giggling like a 14-year-old girl. For a long time, I kind of avoided photographs of people smiling. I never thought I would have a cover with someone with a massive grin on her face, but it just worked. It felt so honest. It was just so joyous.” —Jamie Hawkesworth, Photographer

“This was my first shoot for W. I was inspired by Francis Bacon’s paintings, which seemed photographic to me—the way he would blur motion. Bacon’s work felt very similar to things that I was experimenting with. Alex White, who was the fashion editor on this story, and I really felt that we were pushing some boundaries in fashion photography.” —Mario Sorrenti, Photographer

“This project was centered around the idea of ‘plandids,’ the planned photos that you see on social media that are supposed to look candid. I was kind of just lying around, recovering from an injury, with nothing to do and playing with my phone. I actually hate the idea of selfies. People say, ‘Oh, but you’re, like, the queen of selfies,’ and I really kind of cringe at that thought.” —Cindy Sherman, Artist