Only a handful of red-carpet moments can rise to the level of legendary. For InStyle's 25th birthday, supermodels Amber Valletta, Joan Smalls, and Karen Elson bring new life to 25 unforgettable dresses — as you’ve never seen them before.

By Eric Wilson
Aug 06, 2019 @ 8:00 am
Joan Smalls in the dress worn by Rihanna at the 2015 Grammy Awards. Photo by Sebastian Faena/IMG Lens.

Elizabeth Hurley needed a dress.

Donatella Versace recalls the night, 25 years ago, when the young actress, who was then making headlines as the girlfriend of Hugh Grant, asked to borrow something less than 24 hours before the London première of Four Weddings and a Funeral. As luck would have it, one dress that happened to be available was a black body-hugging gown that Helena Christensen had modeled in Gianni Versace’s spring show; it was trimmed with large gold safety pins to reflect the collection’s punk inspiration, and when Hurley tried it on, the revealing effect flattered her perfectly. The story of the dress that would go on to put both Versace and Hurley on the map, it turns out, was as simple as that.

“I know, you’d expect something more interesting behind one of the most famous red-carpet dresses in history,” Versace says, “but as for many things, chance played a big role in making it all happen. No one could really fathom such an astonishing reaction, or that Liz would steal the spotlight from everyone else.”

VIDEO: 25 Unforgettable Dresses

If there is one thing to be learned from the past quarter century of celebrity fashion covered in InStyle, as the red carpet has evolved from an insider’s trade dominated by a handful of foresighted Italian designers into a highly sophisticated and calculated industry involving a cast of thousands, it is that some dresses are fated to become iconic because they reflect more than just their moment. Take a look at the 25 examples here, each an image that captured the public’s attention in a way that helped tell a story about fashion and beauty — in Versace’s case, that women were beginning to celebrate their bodies and no longer hide them under classic Hollywood gowns.

“People across the globe started talking about the dress,” Versace says. “That’s when we started to realize the power of the red carpet and celebrities in creating topics of conversation.”

When the right dress meets the right star on just the right occasion, even designers recognize something more powerful is happening than just the usual stagecraft. Think of Nicole Kidman at the 1997 Oscars wearing a couture sheath by John Galliano for Dior that was seen as controversial at the time for its unconventional color, chartreuse, and for its chinoiserie embroidery (the dress made Joan Rivers gag). Or Gwyneth Paltrow, the picture of innocence in a cotton-candy-pink dress by Ralph Lauren, when she won best actress for Shakespeare in Love in 1999. Or, more recently, Rihanna arriving at the 2015 Grammy Awards in an enormous cloud of flamingo tulle. Her couture dress by Giambattista Valli, which had been shown on the runway only days before, stood out in aerial photographs of the audience at the Staples Center in Los Angeles, becoming an early example of how a red-carpet moment could set social media on fire.

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“I was mesmerized not only by how well she wore the dress but also by her fresh and effortless beauty,” Valli says. “She looked like she had just taken a shower and zipped up her dress to walk the red carpet.”

The thing is, the dress weighed nearly 18 pounds.

“Every once in a while, a dress and an actress can create a certain kind of magic,” says Vera Wang, whose orange silk chiffon dress worn by Charlize Theron at the 2000 Academy Awards, a potent combination of sexy and sophisticated, remains an all-time favorite of many critics. Theron, having just completed The Legend of Bagger Vance, wanted to evoke a 1930s style with her dress, hairstyle, and accessories, art deco jewelry from Bulgari and diamond clips by Fred Leighton that had to be sewn onto the dress so they would stay in place all evening.

“I loved the halter neckline and ruched front — sensual, graceful, and seductive — but not the easiest dress to sew,” Wang remembers. “Each layer of chiffon was a different color and cut on the bias without any side seams in order to create a certain depth of tonalities. And it took only one fitting!”

Over the past few decades, as the collaborative process has become more important, some of the most memorable looks were the result of personal relationships between celebrities and designers that have developed over many years, like that of Cate Blanchett and Giorgio Armani, or Julianne Moore and Tom Ford, or Natalie Portman and Kate and Laura Mulleavy of Rodarte, who contributed designs for Portman’s ballet scenes in Black Swan. For the Oscars that year, when Portman won best actress during her first pregnancy, the Mulleavys designed her ravishing violet maternity dress with sprinkles of crystals around the neckline.

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“Natalie had wanted to wear an off-the-shoulder gown in a beautiful purple or plum tone,” recall the Mulleavys, who were even thanked in Portman’s acceptance speech. “We watched the ceremony with Natalie’s best friend and cheered every time she was on.”

Each dress has a special story, and some even have secrets.

The extraordinary Prada dress Lupita Nyong’o wore to the 2014 Academy Awards, where she won a supporting actress Oscar for 12 Years a Slave, contains a small panel sewn inside with a frog made of crystals. Her stylist, Micaela Erlanger, had worked closely with Prada to develop a dress as meaningful as the moment — in interviews Nyong’o even described the color as “Nairobi blue.” But the frog was more personal, a totem adopted by her family to represent her great-great-grandfather Nyawang’ Ogwal, who was named after the area where he grew up, which had a wetland full of frogs. Says Erlanger, “She wanted to have the frog represented in her dress as a symbol of having her family close to her.”

Alicia Vikander proves that even the most exquisite creations are not always handled so carefully. Right after leaving the stage of the SAG Awards during her 2016 awards streak for The Danish Girl, she had a flight to catch. Still wearing her gown by Nicolas Ghesquière for Louis Vuitton, which was constructed of thousands of hand-sewn sequins in a geometric pattern of metallics, she boarded the plane. “That dress has had a bit of an adventure,” Vikander says.

And on the night of the 2000 Oscars, the train of Theron’s Vera Wang dress ripped when someone stepped on it at an after party, leaving her potentially exposed until Moore came to the rescue with a safety pin.

Moore reveals another story behind a famous design, the universally acclaimed emerald green strapless Yves Saint Laurent dress Ford created for her for the 2003 Academy Awards. “I was nursing my daughter, Liv, at the time — she was almost a year old — and one side of the dress had to be built out because I had only one breast that would really produce,” she says. “It was the second time I went to the Oscars while I was nursing a baby.”

Speaking of getting something off her chest, Paltrow has this to say about the pink dress, which was somewhat polarizing for its loose-fitting bodice: “I didn’t have a stylist, and I was really young, so I didn’t fully grasp how much time and thought usually goes into choosing an Oscar dress,” she says. “I was so stressed and nervous the week before the Oscars, and I’d lost a ton of weight. When I went to put the dress on, my boobs had basically disappeared, and I thought, ‘Oh no, I can’t fill this out, but I have no other option.’ It was all very accidental.”

The London designer Ben de Lisi remembers the delight he felt when Kate Winslet wore one of his dresses, a red gown with a delicate floral strap, to the 2002 Academy Awards. He was horrified, however, when she revealed during a red-carpet interview that she had to get nearly undressed to use the ladies’ room. He had created a power-mesh undergarment that flattered her figure, but it also constricted her from the knees to the chest. “Nonetheless, it was a small pill to swallow for the accolades I received for months afterward,” he says.

RELATED: The Oscar Dresses We Can't Forget (and Don't Want To!)

There’s no underestimating the pressure celebrities face on the red carpet, even more so now, in the age of social media. In recent years stylists and stars are ever more conscious of how they will be judged, but, paradoxically, red-carpet dressing has only become bolder. When Paltrow wore a white Tom Ford dress and matching cape to the Oscars in 2012, she pushed fashion forward in a way that seemed particularly daring—so much so that her stylist, Elizabeth Saltzman, says she spent weeks imagining all the negative reviews the critics might write.

“Whether it was the ‘caped crusader’ or the ‘ice queen,’ I thought of every terrible thing I could say just to take away any of the fear of what that dress could be,” Saltzman says. “But in the end, when she put on the dress, it was so perfect, it was like you almost didn’t want to open your mouth.”

Now, in the wake of #MeToo and Time’s Up, which put the narratives surrounding fashion and beauty back into the hands of the women wearing the dresses, those women are fearless, says stylist Samantha McMillen. “And that has opened up so many possibilities for women to express themselves,” she says, recalling the moment when she and Elle Fanning chose a dramatic full-length couture gown with a capelet from Valentino’s Pierpaolo Piccioli to make a statement at the Berlin International Film Festival in 2018.

“We were walking back to her hotel room, and I noticed a staircase where I just had to take her picture,” McMillen says. “I felt like maybe we were making history here — not to be pompous about it — but it felt like magic.”

Photographed by Sebastian Faena. Styled by Julia Von Boehm. Sittings editor: Sam Broekema.

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