Every Met Gala look Anna Wintour has worn since she began running the show in 1995

Every Met Gala look Anna Wintour has worn since she began running the show in 1995
  • Anna Wintour, Vogue's editor in chief, has co-chaired nearly every Met Gala since 1995.

  • Wintour, 74, calls the shots, including who gets invited.

  • Ahead of this year's event on Monday, take a look at Wintour's Met Gala stylebook over the years.

It's hard to picture a Met Gala without Anna Wintour.

Since 1995, Vogue's editor in chief has played an integral role in organizing the most talked-about fashion event of the year, founded in 1946 as a fundraiser for the Metropolitan Museum of Art's Costume Institute.

With Wintour, now 74, at the helm, the gala became more extravagant. As the guest list became increasingly star-studded, the prices of coveted tickets skyrocketed from around $2,000 to $50,000.

Author Amy Odell, who wrote "Anna: The Biography," told Grazia in 2016 that Wintour wields considerable control over how the Met Gala runs and, importantly, who gets an invite.

While she doesn't choose the theme, Wintour is known to approve almost every outfit worn on the gala's famous red carpet.

Ahead of this year's event on May 6 — which Wintour will co-chair with Zendaya, Chris Hemsworth, Jennifer Lopez, and Bad Bunny — here is every outfit she's worn for fashion's biggest night.

In 1995, the Met Gala's theme was "Haute Couture." Wintour, who rocked her signature blunt bob, attended in an ivory halterneck gown.

Clarissa Alcock, Anna Wintour, and Annette Reed at the 1995 Met Gala.
Clarissa Alcock, Anna Wintour, and Annette Reed at the 1995 Met Gala.Nick Haddow/Penske Media via Getty Images

For her debut as a Met Gala co-chair, Wintour nailed the straightforward theme of the night in a sleek, silky-looking floor-length white gown with matching opera gloves and minimal jewelry.

The look was refined and elegant, encapsulating the "Haute Couture" theme of the 1995 Met Gala, sponsored by designers Karl Lagerfeld and Gianni Versace.

Wintour did not co-chair in 1996, but she returned the following year wearing a gold dress for the Gianni Versace-themed Met Gala.

Donatella Versace, Elton John, Anna Wintour, and Julia Koch at the 1997 Met Gala.
Donatella Versace, Elton John, Anna Wintour, and Julia Koch at the 1997 Met Gala.Steve Eichner/Penske Media via Getty Images

The 1997 Met Gala paid homage to Gianni Versace, who died after being shot in Miami months prior.

The late designer was known for his love of working with metal embellishments and gold tones, so it's no wonder that Wintour took that on board with her look for the evening: a shimmery, liquid-like gold gown with thin spaghetti straps. She paired it with coordinating stilettos and a sparkly silver necklace.

Wintour kept things simple in a slip dress for the 1998 Met Gala, which was themed "Cubism and Fashion."

Anna Wintour at the 1998 Met Gala.
Anna Wintour at the 1998 Met Gala.Steve Eichner/WWD/Penske Media via Getty Images

Wintour's look, a lightweight gold slip dress paired with a silver necklace and two bracelets, didn't exactly scream "Cubism and Fashion."

But, in Wintour's defense, the trend of wearing an outfit that nodded to the Met Gala theme wasn't huge at the time.

In 1999, Wintour blurred the lines between high fashion and punk rock for the "Rock Style"-themed Met Gala.

Andre Leon Talley and Anna Wintour at the 1999 Met Gala.
Andre Leon Talley and Anna Wintour at the 1999 Met Gala.Rose Hartman/Getty Images

In 1999, Wintour graduated from being a standard co-chair to officially taking the reins as the Met Gala's chairperson. That year, the theme was "Rock Style," highlighting how iconic performers like Elvis Presley, Aretha Franklin, and Alice Cooper, among others, influenced style trends.

Unlike the previous year, Wintour didn't shy away from the theme. Her eclectic John Galliano couture look consisted of a purple embellished skirt with a patterned white top layered under a tanned fur stole.

Wintour channeled Jackie Kennedy's preppy yet elegant style at the 2001 Met Gala that paid tribute to the former first lady.

Anna Wintour and a friend at the 2001 Met Gala.
Anna Wintour and a friend at the 2001 Met Gala.Steve Eichner/WWD/Penske Media via Getty Images

The 2000 Met Gala failed to go ahead after an exhibit on the works of Coco Chanel was canceled, but the event returned in 2001 with a gala dedicated to the late Jacqueline "Jackie" Kennedy Onassis and her fashion legacy. The former first lady is remembered for her sophisticated wardrobe that included vibrant dresses, pillbox hats, turtleneck long sleeves, and chic evening gowns.

Wintour arrived at the Met that year in a timeless ensemble: a floor-length gown comprised of a classic flowing white skirt and a shimmery baby-blue, high-neck top with floral embellishments and shoulder pads.

The 2003 Met Gala's theme was "Goddess: The Classical Mode." Wintour arrived in an angelic Christian Dior ensemble.

Anna Wintour at the 2003 Met Gala.
Anna Wintour at the 2003 Met Gala.Evan Agostini/Getty Images

Wintour's ethereal Christian Dior look was perfect for the 2003 Met Gala's "Goddess: The Classical Mode" theme, the first held after a hiatus in 2002 following the 9/11 attacks.

The Vogue editor's look consisted of a silky floor-length loose white gown paired with silver strappy stilettos and a cropped fringed shawl-style cardigan.

Her final accessory? Wintour's iconic black sunglasses, which she later told CNN she likes to wear to "avoid people knowing what [she's] thinking about."

She wore one of her quirkiest Met Gala looks to date for the 2004 "Dangerous Liaisons: Fashion and Furniture in the 18th Century"-themed event.

Anna Wintour, dressed in a sparkling jacket and pale green full-length gown, poses in front of photographers during the 2004 Met Gala.
Anna Wintour at the 2004 Met Gala.Evan Agostini/Getty Images

Wintour partnered with Christian Dior again for her look at the 2004 Met Gala. She wore a pastel-green silk dress embellished around the neckline, which she paired with a crystal-encrusted jacket with exaggerated shoulder pads.

The look is one of the most eclectic that Wintour has worn to the Met Gala throughout the years, but it was in line with the theme of the year, which focused on the "refined elegance and delicate voluptuousness" of interiors and style during the 18th century, according to the Metropolitan Museum website.

The fashion editor wore a silky white gown with a floral-embellished cardigan for the 2005 "House of Chanel"-themed Met Gala.

Anna Wintour at the 2005 Met Gala.
Anna Wintour at the 2005 Met Gala.Evan Agostini/Getty Images

Wintour stayed on theme in an asymmetrical white Coco Chanel gown and a coordinating cardigan with floral appliqués. She accessorized with silver heels and a statement pearl necklace with a fringed pendant.

The 2006 Met Gala was all about honoring British fashion, a perfect theme for Wintour, who was born in London.

Anna Wintour at the 2006 Met Gala.
Anna Wintour at the 2006 Met Gala.Evan Agostini/Getty Images

"AngloMania: Tradition and Transgression in British Fashion" was the theme of the 2006 Met Gala.

While Wintour opted not to work with a British designer on her look for the evening, instead choosing Chanel, her ensemble oozed English elegance. It consisted of a black sequined gown with pink rose details along the train and chest, and a flowing beige coat — perhaps a high-fashion nod to the iconic Burberry trench coat.

Wintour went for an edgy look at the 2007 Met Gala in a black sequin-heavy ensemble with scale-like detailing.

Anna Wintour at the 2007 Met Gala.
Anna Wintour at the 2007 Met Gala.Evan Agostini/Getty Images

In 2007, the Met Gala theme was "Poiret: King of Fashion," in honor of Paul Poiret, a designer famous for influencing the transition in women's fashion from corsets to looser clothing items.

For the event, Wintour wore a sequined Chanel gown with a segment of black and white scales embroidered down the center and on the shoulders.

She embodied power and fashion at the 2008 "Superheroes: Fashion and Fantasy" Met Gala.

Anna Wintour at the 2008 Met Gala.
Anna Wintour at the 2008 Met Gala.Stephen Lovekin/Getty Images

Wintour arrived on the red carpet in a silver Chanel gown designed by Karl Lagerfeld. The dress featured shell-shaped padding along the waist and shoulders.

The ensemble looked like it could've been pulled from the costume department of an epic sci-fi movie, proving she nailed the event's fantasy theme.

For the 2009 Met Gala, themed "The Model As Muse: Embodying Fashion," Wintour went for a black-and-white number.

Anna Wintour at the 2009 Met Gala.
Anna Wintour at the 2009 Met Gala.Billy Farrell/Patrick McMullan/Getty Images

Chanel designed her white dress, featuring a black oval pattern.

While it was one of the safer looks Wintour has worn to the Met Gala, it featured a few playful details, such as pointed shoulders and a thick black belt.

Wintour dazzled at the 2010 Met Gala in a silver-tiered Chanel dress.

Anna Wintour at the 2010 Met Gala.
Anna Wintour at the 2010 Met Gala.Kevin Mazur/WireImage

She paired the silver Chanel dress with a sequin-heavy silver jacket and a necklace.

While elegant, it isn't Wintour's most on-theme Met Gala look of all time, given the event was themed "American Woman: Fashioning a National Identity."

In 2011, Wintour wore an ombré sequined dress that paid tribute to Alexander McQueen.

Anna Wintour at the 2011 Met Gala.
Anna Wintour at the 2011 Met Gala.Kevin Mazur/WireImage

The theme for the 2011 Met Gala was "Alexander McQueen: Savage Beauty," in honor of the late British designer known for his originality and meticulous tailoring.

Honing in on McQueen's mastery of tailoring, Wintour opted for a fitted Chanel gown decorated with tiny multicolored sequins to recreate a bold ombré pattern. It also had a section of gold sequins running down the center.

She looked glamorous at the 2012 Met Gala that honored not one but two iconic fashion houses.

Anna Wintour at the 2012 Met Gala.
Anna Wintour at the 2012 Met Gala.Stephen Lovekin/FilmMagic

The 2012 Met Gala's theme paid tribute to two iconic Italian designers: Elsa Schiaparelli and Miuccia Prada.

In line with "Schiaparelli and Prada: Impossible Conversations," Wintour chose to wear a textured white Prada gown with a white fur stole.

The dress may have been Prada, but that doesn't mean Wintour forgot about Schiaparelli. Her gown featured a large gold lobster, a not-so-subtle nod to the "lobster dress" Elsa Schiaparelli made in 1937.

Wintour put a playful, feminine spin on the 2013 Met Gala theme, "Punk: Chaos to Couture."

Anna Wintour at the 2013 Met Gala.
Anna Wintour at the 2013 Met Gala.Jennifer Graylock/FilmMagic

Wintour wore a floral Chanel dress with white stilettos.

To the untrained eye, the gown might not scream "punk," but the DIY-inspired pattern and the fact that a couture house created the dress nailed the theme.

The 2014 Met Gala was themed "Charles James: Beyond Fashion," to which Wintour wore a ball gown covered in floral appliqués.

Anna Wintour at the 2014 Met Gala.
Anna Wintour at the 2014 Met Gala.Dimitrios Kambouris/Getty Images

Wintour's Chanel gown had a sheer neckline and featured an array of red, blue, beige, and black flower petal appliqués. She accessorized with gold heels and a chunky silver necklace.

The ball gown was in line with the theme of the night, which paid tribute to the late designer Charles James, who was known for his "sculptural" and "scientific" approach to dressmaking, according to the Metropolitan Museum website.

"China: Through the Looking Glass" was the 2015 Met Gala theme. Wintour arrived in an orange-and-red floral gown.

Anna Wintour at the 2015 Met Gala.
Anna Wintour at the 2015 Met Gala.Larry Busacca/Getty Images

The dress, designed by Chanel, was covered in varying-sized floral appliqués in orange and red hues.

Wintour's color palette for the night was a subtle nod to the theme of the evening, "China: Through the Looking Glass."

Wintour wore an intricately beaded white gown with fringed sleeves for the 2016 Met Gala.

Anna Wintour at the 2016 Met Gala.
Anna Wintour at the 2016 Met Gala.Dimitrios Kambouris/Getty Images

Joining forces with Chanel for yet another Met Gala, Wintour arrived on the red carpet in a floor-length beaded gown with fringe detailing along the sleeves and train and light-brown feathers stitched around the chest.

The intricate detail throughout the dress paid tribute to the "Manus x Machina: Fashion in an Age of Technology" theme, which delved into how fashion designers create through their handiwork and machinery.

In 2017, she wore a gold-embellished gown with a playful feathery segment and a sheer train.

Anna Wintour at the 2017 Met Gala.
Anna Wintour at the 2017 Met Gala.Kevin Mazur/WireImage

The 2017 Met Gala was themed after Rei Kawakubo, a Japanese designer known for challenging classic silhouettes by playing with asymmetry and dress construction.

For the event, Wintour honored the theme and Kawakubo by wearing a technically adventurous Chanel gown that featured heavy embellishments, a feathery white skirt, and a semi-sheer train.

Wintour wore a semi-sheer silver dress with sleek cutouts and accessorized with a rosary at the "Heavenly Bodies"-themed Met Gala in 2018.

Anna Wintour at the 2018 Met Gala.
Anna Wintour at the 2018 Met Gala.ANGELA WEISS/AFP via Getty Images

The 2018 Met Gala theme, "Heavenly Bodies: Fashion and the Catholic Imagination," is among the most popular in recent history.

Wintour served a master class in abiding by the dress code when she arrived in a silver Chanel halterneck gown overlayed with a sheer cream fabric that had two delicate cutouts around the neck. The best part of her look had to be her dark silver rosary, which fit the theme perfectly.

The 2019 Met Gala was all about camp fashion, and Wintour delivered.

Anna Wintour at the 2019 Met Gala.
Anna Wintour at the 2019 Met Gala.Jamie McCarthy/Getty Images

The 2019 Met Gala's theme, "Camp: Notes on Fashion," was about bold, exaggerated, playful looks.

Wintour, wearing Chanel again, nailed the assignment in a pink gown covered in pastel flowers and a coordinating pink-and-purple feathery stole.

Her outfit won the praise of Rihanna, who wrote on X that Wintour was the "best dressed" attendee of the Met Gala that year, E! News reported.

Following a yearlong hiatus during the COVID-19 pandemic, the Met Gala returned with force in 2021 — and so did Wintour's fashion.

Anna Wintour at the 2021 Met Gala.
Anna Wintour at the 2021 Met Gala.Mike Coppola/Getty Images

"In America: A Lexicon of Fashion" was the 2021 theme of the Met Gala, paying tribute to the evolution of fashion and culture in the US.

Wintour broke from her tradition of wearing Chanel by choosing an Oscar de la Renta dress. Boldly printed with sunflowers, lilacs, and posies, the long-sleeved dress featured ruffles along the train and neckline.

She returned to wearing Chanel at the 2022 Met Gala, emphasizing "Gilded Glamour."

Anna Wintour at the 2022 Met Gala.
Anna Wintour at the 2022 Met Gala.Jeff Kravitz/FilmMagic

It seems that Wintour and Chanel cannot be separated for longer than a year. In 2022, for the "Gilded Glamour" dress code, the Vogue editor in chief opted for a rainbow-colored dress embellished with tiny beads.

She added a touch more glamour with a coordinating feathery poncho.

The 2023 Met Gala honored the late Karl Lagerfeld, so it made sense that Wintour wore Chanel.

Anna Wintour and Billy Nighy attend the 2023 Met Gala.
Anna Wintour and Bill Nighy attend the 2023 Met Gala.Jamie McCarthy/Getty Images

Lagerfeld, who died in February 2019 at age 85, was a fashion juggernaut best known for serving as the creative director of Chanel.

Paying tribute to the designer, whom she was close friends with for decades, Wintour attended the 2023 Met Gala in a white skirt and a sparkly sequined pattern coat designed by Chanel.

She also arrived alongside actor Bill Nighy, briefly stirring up romance rumors until his spokesperson told People they are simply "great friends."

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