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From Princess Diana to Beyoncé — Looking Back at 25 Years of Iconic Met Gala Moments

Lady Gaga at the 2019 Met Gala. Photo: Theo Wargo. Wireimage

Remember Kate Moss’s Met Gala debut, dressed in a minimalist Calvin Klein dress? What about Princess Diana, who stole the show in 1996? Or, when Cher bared (nearly) all in a sheer Bob Mackie gown? In honor of the Met Gala’s landmark 25th anniversary, this is your recap of the iconic fashion moments that defined the world’s most powerful red carpet.

1. Lady Gaga in Brandon Maxwell (2019)

You can always count on Lady Gaga to make a sensational (in this case, 16 minute) Met Gala entrance. For Celebrating Camp: Notes on Fashion, the superstar wore an enormous fuchsia cape coat (25 yards of fabric, to be precise), created by her longtime friend and collaborator Brandon Maxwell. The drama did not end there. Over the course of her live red-carpet performance, the cape was unfastened to reveal a black strapless bustier gown. Which was, in turn, shed to showcase a shocking-pink gown. Which was then removed to unveil a sparkling bra and knickers. “I know intrinsically that I have a camp soul,” she told Vogue while getting ready for the big event.

Photo : New York Daily News. Getty Images

2. Diana, Princess of Wales, in Dior (1996)

Princess Diana made her one and only appearance at the Met Gala in 1996, three months after news of her divorce from Prince Charles was first made official. By today’s red carpet standards — and the Met Ball’s empowered ‘naked dress’ phenomenon — Princess Diana’s look could be mistaken as demure, but this navy blue lingerie gown, a Dior classic designed by then creative director John Galliano, signaled a new, liberated moment. The 1996 Gala honored the legacy of Christian Dior, and naturally Galliano himself was on hand to escort the Princess of Wales around the Met, alongside former British Vogue editor-in-chief Liz Tilberis. We also can’t ignore the jewelry: a seven-stranded pearl choker necklace, with an enormous sapphire and diamond clasp.

Photo: Rabbani and Solimene. Getty Images

3. Rihanna in Guo Pei (2015)

We were torn between the superstar’s 2017 Comme des Garçons petal dress and the 2015 “omelette” cape-cum-gown by Chinese couturier Guo Pei, but for sheer impact — a 16-foot train, to be precise — the one-of-a-kind yellow cape wins. RiRi stole the show (and arguably the entire year in style), nailing the China: Through the Looking Glass theme in one fabulous fell swoop, with a piece weighing in at 25kg, which took more than two years to create. The Pei-RiRi partnership has since become the modern benchmark for how a designer, little known outside her home country, can become a worldwide Vogue sensation before the sun has set on the first Monday in May.

Photo : Dia Dipasupil. Filmmagic

4. Billy Porter in The Blonds (2019)

Pose star Billy Porter knows a thing or two about a show-stopping red carpet appearance. The Broadway stalwart’s First Monday in May moment saw him arriving in a sedan chair, carried atop the shoulders of six bare-chested men in an homage to Elizabeth Taylor’s Cleopatra. The main event? A custom “Sun God” catsuit with 10ft wings, designed by The Blonds.

Photo: Ron Gallela. Wireimage

5. Bianca Jagger in Halston (1977)

When American designer Halston launched his eponymous clothing line in 1966, the Parisian fashion establishment was shaken. His was an accessible, unruly glamour worn by a decadent girl gang of ‘Halstonettes’ including Bianca Jagger, his date for the 1977 Gala (theme: Vanity Fair: A Treasure Trove) where New York’s explosive downtown scenesters and well-heeled uptown crowd mingled in the halls of the Met. Jagger wore a Halston halter-neck metallic dress with matching shawl and drawstring evening bag with an overtly disco edge. There was only one after-party destination: a new nightclub called Studio 54.

Photo : John Shearer. Getty Images

6. Cardi B in Thom Browne (2019)

“I chose Thom Browne because he is the definition of camp,” Cardi B told Vogue as she prepared for the Met Gala red carpet. The look? A hand-embroidered oxblood gown festooned with 30,000 burned and dyed coque feathers, which reportedly took 35 people more than 2,000 hours to create.

Photo: Dia Dipasupil. Getty Images

7. Diddy and Cassie (2017)

The Met Gala has a tradition of attracting extraordinary celebrity couplings (remember Donatella Versace and Matt Dillon in 1999?) and a knack for conjuring famous duos that don’t ordinarily court red-carpet attention. In 2017, Diddy (aka Sean Combs) wasn’t hung up about posing in front of the flashbulbs, preferring instead to recline on the Met Museum steps while then-girlfriend Cassie Ventura did her thing in a tiered On Aura Tout Vu gown. The upshot? Diddy did away with traditional red-carpet etiquette and made Met Gala magic in the process.

Photo: Ron Gallela. Wireimage

8. Jackie Onassis in Valentino (1979)

Rewind to the Fashions of the Hapsburg Era-themed gala in 1979, when Jackie Onassis wore a black, strapless Valentino silk gown with matching capelet and a jewelry-free décolletage that would make today’s red-carpet minimalists proud. The unflashy fashion mood wasn’t just a one-night thing, but rather established the style that would take her through the final chapter of her life as a book editor in Manhattan, after returning to live in the US following the death of her second husband, Greek shipping magnate Aristotle Onassis.

Photo: Ron Gallela. Wireimage

9. Naomi Campbell in Versace (1995)

Back in the pre-Instagram dark ages of 1995, when 2017 Met Gala essential KiraKira wasn’t even a twinkle in an app developer’s eye, Naomi Campbell sported a radiant, crystal-encrusted Versace column gown capable of blinding over-eager paparazzi. The impossibly glittering creation — a Gianni Versace masterpiece — found a perfect match in supermodel Naomi, who 25 years on, reigns more powerfully than ever.

Photo : Patrick McMullan. Getty Images

10. Kate Moss and Marc Jacobs (2009)

As far as dream Met Gala wingmen go, few can top Marc Jacobs. The designer accompanied BFF Kate Moss in 2009, when the supermodel wore a burnished metallic minidress and matching head wrap — both by Marc Jacobs. (File the coordinating shoes, custom YSL tributes, under ‘most powerful footwear of the 2000s’.) That year’s theme? The Model as Muse, which Moss had in the bag.

Photo by Karwai Tang . Wireimage

11.Katy Perry in Moschino (2019)

If there’s one designer who knows how to unleash a theatrical (and witty) Met Gala moment, it’s Moschino creative director Jeremy Scott. The camp look he created for his friend, singer Katy Perry, featured a built-in corset with two hidden battery packs to illuminate the chandelier’s lights. “Who has ever been to a ball that did not have a chandelier?!” Scott deadpanned with Vogue.

12. Liv Tyler and Stella McCartney (1999)

Rock’n’roll offspring Liv Tyler and Stella McCartney flouted red-carpet convention in 1999, wearing custom “Rock Royalty” tees, which spelt out both the Gala’s theme (Rock Style) and their gilded lineage. The mischievously pared-down style move, which would probably still cause a stir today, triggered an instant DIY-look trend that would rule the high street for seasons to come (one-shoulder necklines included).

Photo: Theo Wargo. Wireimage

13. Kylie and Kendall Jenner in Versace (2019)

How do two of social media’s most famous family prepare for the world’s stage? They mastermind feather-trimmed Versace gowns in zinging shades. Kylie Jenner, who also arrived alongside Travis Scott, went all-in, topping off her tonal lilac look with a coordinating lavender wig. The clashing-hues of this particular Jenner duo also dialed in the sister’s personal, off-camera style. Kylie had initially tried to persuade Kendall to wear pink, instead of orange, for a more matching look. “I was trying to convince her to do pink… but she’s not a pink girl, so she says,” Jenner told Vogue. The result? A wholly individual homage to showgirl camp.

Photo: Kevin Mazur. Wireimage

14. Sarah Jessica Parker in Oscar de la Renta (2014)

No Met Gala greatest hits roundup would be complete without The Sex and the City star. Our favorite? The sweeping Oscar de la Renta gown Parker wore to the 2014 Met Gala, honouring Anglo-American couturier Charles James, which is worthy of a Carrie Bradshaw finale sequence. That particular night was a big deal for both de la Renta and Parker, who were the event’s co-chairs. The actress’s look was a longtime labour of love, which the designer built from scratch especially for the occasion. The detail you may have missed? The dress’s black trellis motif featured de la Renta’s signature in scarlet embroidery, ‘sealing’ the eternal friendship of the designer and the muse.

Photo: Ron Gallela. Wireimage

15. Cher in Bob Mackie (1974)

Decades before Kendall Jenner bared all in a bespoke crystalline dress by La Perla, Cher attended the second-ever Met Ball wearing a risqué custom feather-trim gown by Bob Mackie, her go-to costume designer. The singer’s shimmering cobweb dress kickstarted the Met’s ‘naked dress’ phenomenon and gave rise to a slew of homages, including the Roberto Cavalli gown Kim Kardashian West wore in 2015, Beyoncé’s legendary Givenchy by Riccardo Tisci moment (also in 2015) and Madonna’s thong-backed lace dress (also Givenchy) in 2016.

Photo : Erik Pendzich. Shutterstock

18. Beyoncé in Givenchy by Riccardo Tisci (2015)

Where Beyoncé goes, the rest of us follow. For the star’s former stylist Ty Hunter at the 2015 gala that meant literally following her. Beyoncé’s jewel-encrusted Givenchy Haute Couture by Riccardo Tisci dress required special care and attention, demanding Hunter was on hand (or, rather, knees) to make sure it was perfectly positioned for each flawless red-carpet shot.

Photo: Evan Agostini. AP/Invision/Shutterstock

19. Lizzo in Marc Jacobs (2019)

It’s impossible to spotlight Lizzo’s decadently feathered Marc Jacobs look, which shutdown the 2019 red carpet (and after party) without also crediting the fact that the musician went straight to the airport the next day, accessorising the Barbie-pink, floor-sweeping feather coat with a cropped sweater, dressed-down trousers and heavy-duty sunglasses in Virgin Atlantic’s Upper Class lounge.

Photo: Ron Gallela. Wireimage

20. Kate Moss in Calvin Klein (1995)

The supermodel’s first-ever appearance at the Met Gala is one for the fashion history books. The theme of the 1995 gala was Haute Couture, but in classic Moss-style, she elected to go for a straightforward, knockout gown. No pomp, no train, no fuss; this buttermilk design is Calvin Klein, and isn’t it just perfect?

Photo: Rob Latour. Shutterstock

21. Sarah Paulson and Madonna (2017)

Sometimes even celebrities get starstruck, as demonstrated by actress Sarah Paulson, who cast off outdated red-carpet protocol at the 2017 Met Gala red carpet to fangirl Madonna and her now infamous camouflage Moschino dress.

Photo : Dimitrios Kambouris. Getty Images

22. Kanye West and Kim Kardashian West (2016)

If Kanye wants to (controversially) wear ripped ice-blue Fear Of God jeans and matching ice-blue contact lenses to the Met Gala, he will. Even if the dress code states “tech white tie”. Kanye’s glitzy jacket? Balmain. Kim’s glitzy dress? Balmain. The 2016 theme? Manus x Machina. The superstar wasn’t the last star to wear denim on the Met red carpet, however. A$AP Rocky did full-look Calvin Klein denim in 2017 to wide-sweeping acclamation from the fashion world.

Photo : David X Prutting / BFA /Shutterstock

23. Lupita Nyong’o in Prada (2014)

Feather trims have been a longstanding part of the Met Ball fashion vocabulary — Julianne Moore, Rita Ora, Kirsten Dunst and Blake Lively have all worn cocktail-hour plumage on the Gala’s red carpet — but it’s Lupita Nyong’o’s custom Prada gown from the 2014 Charles James: Beyond Fashion themed gala that takes the prize. Styled by Micaela Erlanger, this was ornithological theatrics with a flapper twist; an emerald mesh dress decorated with crystals and paired with matching shoes and headband. Nyong’o’s Vogue cover-girl composure and the simple minidress she sported beneath completed the look.

Read Next: Yes, You Can Actually Watch the 2021 Met Gala This Year—Here’s How

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