Anna Wintour (Photo by Ron Galella/Ron Galella Collection via Getty Images)
This is Anna's first year atop Vogue. The theme here was "From Queen to Empress: Victorian Dress," but back then I don't think the theme was quite so entwined with the party itself. Not that it would have mattered to A-Dubs. Perhaps all the black here was an ode to Queen Vic herself, who mourned Albert so wholeheartedly. Sure.
1989
NEW YORK, NY : CIRCA 1989: Anna Wintour attends the Annual Costume Institute Exhibition Gala (1989) at the Metropolitan Museum of Art circa 1989 in New York City. (Photo by Barbara Rosen/IMAGES/Getty Images)
"Yes, little people, mill round and ignore me all you like. One day I will own you all."
1990
This was "Théâtre de la Mode – Fashion Dolls: The Survival of Haute Couture," and that is a whole lot of words. This is also so BOLD
1993
Calvin Klein, S.I. Newhouse and Anna Wintour during Opening "Diana Vreeland Immoderate Style" Benefit The Costume Institute at Metropolitan Museum of Art in New York City, New York, United States. (Photo by Ron Galella/Ron Galella Collection via Getty Images)
This was "Diana Vreeland: Immoderate Style" and I decided she didn't care that much about paying homage to her predecessor. This may not be true but I like to propose the most dramatic explantion.
1994
Anna Wintour and David Schaffer during 1994 Annual Costume Institute Benefit at Metropolitan Museum of Art in New York City, New York, United States. (Photo by Ron Galella/Ron Galella Collection via Getty Images)
Get ready. This was "Orientalism: Visions of the East in Western dress." Yikes. Also, that is Bee's father, David, and yes, Anna is doing the thick pantyhose thing. I assume after Kate and Meghan both got calls from her about how to navigate them with minimal laddering.
1996
Mandatory Credit: Photo by Fairchild Archive/Penske Media/Shutterstock (6905807a)
Vogue editor Anna Wintour attends the opening night celebration of the Christian Dior exhibition at the Metropolitan Museum of Art.
Costume Institute Gala 1996, New York
The theme this year was Dior, but I don't know if she also wore Dior. It's certainly very pretty on her, though the sunglasses are hilarious. Wintour's gonna Wintour.
1999
Mandatory Credit: Photo by Fairchild Archive/Penske Media/Shutterstock (6906577a)
Anna Wintour in Christian Dior, Aerin Lauder in Oscar de la Renta and Tommy Hilfiger attend the Costume Institute's homage to Rock Style, chaired by Lauder, Hilfiger and Wintour at the Metropolitan Museum of Art on December 7, 1999 in New York...Article title: 'Eye: Electric Ladyland'..1999-12-07
Metropolitan Museum of Art Costume Institute Gala, New York
We skip a few years here, and I don't know why, as they didn't cancel. Archives are finicky things. Anyway, we leap to ROCK STYLE, which she co-chaired with the here-pictured Aerin Lauder and Tommy Hilfiger, none of them looking especially rock. I guess Anna's furs remind me of something Russell Brand might have worn in his Get Him To The Greek phase.
1999
Editor-at-large Andre Leon Talley and Editor-in-chief Anna Wintour attend the Costume Institute gala at the Metropolitan Museum of Art, New York, New York, 1999. (Photo by Rose Hartman/Getty Images)
I threw in this picture for Andre Leon Talley's coat, the conspiratorial glee on their faces, and the fact that they must no longer be speaking given that he's trying to peddle a book that isn't complimentary to her.
2001
Anna Wintour and guest during 'Jacqueline Kennedy: The White House Years' Costume Institute Gala at Metropolitan Museum of Art in New York City, New York, United States. (Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images)
There was no gala in 2000. Jessica is covering the hows and whys of that later, so I'll just leave you with a very cranky Anna picture of a dress that works pretty well on her.
2003
Mandatory Credit: Photo by Fairchild Archive/Penske Media/Shutterstock (6054723b)
(L-R) Anna Wintour and designer Tom Ford attend the Costume Institute Benefit Gala: 'Party of the Year' at the Metropolitan Museum of Art in New York City.
2003 Met Costume Institute Gala, New York
Also no gala in 2002, because of 9/11. Ana and her fresh highlights seem very happy to have gotten back in the swing of things, and I believe this Chanel begins her streak of wearing MOSTLY Chanel.
2003
Mandatory Credit: Photo by Fairchild Archive/Penske Media/Shutterstock (6054723e)
(L-R) Anna Wintour and designer Tom Ford attend the Costume Institute Benefit Gala: 'Party of the Year' at the Metropolitan Museum of Art in New York City.
2003 Met Costume Institute Gala, New York
It was better with the fur on. (Tom Ford up there and Nicole Kidman were the co-chairs.)
2004 in Dior
Mandatory Credit: Photo by Fairchild Archive/Penske Media/Shutterstock (6054741t)
Anna Wintour attends the 'Dangerous Liaisons: Fashion and Furniture in the 18th Century' Costume Institute gala at the Metropolitan Museum.
2004 Met Costume Institute Gala, New York
This was "Dangerous Liaisons: Fashion and Furniture in the 18th Century," to which Anna hs gone as an extremely opulent chair.
2004
Mandatory Credit: Photo by Fairchild Archive/Penske Media/Shutterstock (6054741hb)
Bee Shaffer attends the 'Dangerous Liaisons: Fashion and Furniture in the 18th Century' Costume Institute gala at the Metropolitan Museum.
2004 Met Costume Institute Gala, New York
I don't know if Bee started attending this year, or if it's just the first one for which we have a photo of her. She was 16-going-on-17 at the time, innocent as a rose, but fortunately PRESUMABLY there were no Nazi telegram boys there to try and turn her head.
2005 in Chanel
Mandatory Credit: Photo by Fairchild Archive/Penske Media/Shutterstock (6065693qj)
Vogue's Anna Wintour attends the Metropolitan Museum of Art's annual Costume Institute gala.
2005 Met Costume Institute Gala, New York
This theme was, wait for it, HOUSE OF CHANEL -- Kidman co-chaired it again, apparently after 2004 had no co-chairs; were there no other celebrities in 2003 and 2005? -- and so Anna was right on point in her dress by the House of Chanel. Presumably this event ALSO did not have any Nazi telegram boys present, though it could have, due to Coco Chanel's background. I'm guessing they ignored that part.
2005
Mandatory Credit: Photo by Fairchild Archive/Penske Media/Shutterstock (6065693bg)
Bee Shaffer (L) and mother Anna Wintour attend the Metropolitan Museum of Art's annual Costume Institute gala.
2005 Met Costume Institute Gala, New York
The back of that dress is cumbersome.
2005
Mandatory Credit: Photo by Fairchild Archive/Penske Media/Shutterstock (6065693of)
Bee Shaffer attends the Metropolitan Museum of Art's annual Costume Institute gala.
2005 Met Costume Institute Gala, New York
For the second year in a row, Bee was stuck with a heavy strapless dress that has a seam across her knees/thighs and a big old black splotch between her boobs. This one makes her look like a stained fainting couch. She deserved better.
2006 in Dior for "AngloMania: Tradition and Transgression in British Fashion"
Mandatory Credit: Photo by Fairchild Archive/Penske Media/Shutterstock (6068769jf)
Anna Wintour attends the Metropolitan Museum of Art's annual Costume Institute gala.
2006 Met Costume Institute Gala, New York
Well, that DOES look super on her.
2006
Mandatory Credit: Photo by Matt Baron/BEI/Shutterstock (585676c)
Anna Wintour and Bee Shaffer
COSTUME INSTITUTE GALA CELEBRATING ANGLOMANIA: TRADITION AND TRANSGRESSION IN BRITISH FASHION AT THE METROPOLITAN MUSEUM OF ART, NEW YORK, AMERICA - 01 MAY 2006
It's also highly Extra with the coat on. Bee's fortunes here have also improved.
2007 in Chanel for "Poiret: King of Fashion"
Mandatory Credit: Photo by Matt Baron/BEI/Shutterstock (662256mt)
Anna Wintour
'Poiret: King of Fashion' Costume Institute Gala at The Metropolitan Museum of Art, New York, America - 07 May 2007
May 7, 2007: New York, NY
Anna Wintour .
2007 Metropolitan Museum of Art Costume Gala
Metropolitan Museum of Art
Photo ® Matt Baron/BEImages
I really, really wish this had been Poirot: King of Fashion.
2007
This is a stunning color.
2008 in Chanel
Mandatory Credit: Photo by Kristen Somody Whalen/Penske Media/REX/Shutterstock (6056607r)
Vogue's Anna Wintour attends the Metropolitan Museum of Art's annual Costume Institute gala in New York City. Wintour wears Chanel Haute Couture.
Met 2008 Costume Institute Gala, New York
For "Superheroes: Fashion and Fantasy," Anna seems to have dressed as some kind of communications device in Superman's Cave of Solitude.
2008 in Nina Ricci
Mandatory Credit: Photo by Erik Pendzich/Shutterstock (763276cu)
Bee Shaffer
'Superheroes: Fashion and Fantasy' Costume Institute Gala at The Metropolitan Museum of Art, New York, America - 05 May 2008
The Metropolitan Museum of Art hosted it's annual Costume Institute Gala on 5th May 2008 with Honorary Chair Giorgio Armani and Co-Chairs George Clooney, Julia Roberts and Anna Wintour. This year's theme is 'Superheroes: Fashion and Fantasy', exploring the symbolic and metaphorical associations between fictional characters and fashion in an exhibition at the Museum from May 7 through September 1 2008. The exhibition features approximately 60 ensembles including movie costumes, avant-garde haute couture, and high-performance sportswear to reveal how the superhero serves as the ultimate metaphor for fashion and its ability to empower and transform the human body. The exhibition is made possible by Giorgio Armani with additional support provided by Condé Nast. https://www.metmuseum.org/press_room/full_release.asp?prid=D60AEAE1-EB1D-47CE-AC3C-B6677363958D
Off-theme, but hella dreamy.
2009 in Chanel for "The Model as Muse"
Mandatory Credit: Photo by Charles Sykes/Shutterstock (918361du)
Anna Wintour
'The Model as Muse: Embodying Fashion' Benefit Gala at the Metropolitan Museum of Art Costume Institute, New York, America - 04 May 2009
Last night saw the glamorous and the glorious put on their glad rags and head down to one of the biggest events in the US fashion industry calendar the Met Costume Institute Gala. With a theme of Model As Muse, the night was sponsored by Marc Jacobs who was the star guest of the evening and was accompanied by his main muse of the evening, Kate Moss. Although the number of tickets sold was down on last year, those that rebuffed the credit crunch were treated to a rich array of the most famously beautiful models in the world. Marc Jacobs dressed Kate Moss (a gold lame backless, one shouldered mini dress with a matching turban) and Victoria Beckham (a pink mini dress with black polka dots and a long train) while Louis Vuitton kitted out Madonna with a turquoise ruched mini dress with puffed skirt, thigh-high black boots, jewelled black fingerless gloves and a hair piece tied around a top knot to complete the odd 80s-inspired look.
I like this on her. But I wouldn't have been surprised if she'd turned around and revealed that it's just a fake and she's wearing black pants.
2009 in Nina Ricci
Mandatory Credit: Photo by Matt Baron/BEI/Shutterstock (918329cq)
Bee Shaffer
'The Model as Muse: Embodying Fashion' Benefit Gala at the Metropolitan Museum of Art Costume Institute, New York, America - 04 May 2009
Last night saw the glamorous and the glorious put on their glad rags and head down to one of the biggest events in the US fashion industry calendar the Met Costume Institute Gala. With a theme of Model As Muse, the night was sponsored by Marc Jacobs who was the star guest of the evening and was accompanied by his main muse of the evening, Kate Moss. Although the number of tickets sold was down on last year, those that rebuffed the credit crunch were treated to a rich array of the most famously beautiful models in the world. Marc Jacobs dressed Kate Moss (a gold lame backless, one shouldered mini dress with a matching turban) and Victoria Beckham (a pink mini dress with black polka dots and a long train) while Louis Vuitton kitted out Madonna with a turquoise ruched mini dress with puffed skirt, thigh-high black boots, jewelled black fingerless gloves and a hair piece tied around a top knot to complete the odd 80s-inspired look.
This is so Nina Ricci for Victoria's Secret. It's neither glam nor sophisticated.
2010, "American Woman: Fashioning a National Identity"
Mandatory Credit: Photo by Marion Curtis/Starpix/Shutterstock (5633996ao)
Anna Wintour and Bee Shaffer
Costume Institute Gala Benefit 'American Woman: Fashioning a National Identity', Metropolitan Museum of Art, New York, America - 03 May 2010
Everyone looks fine here. Actually, Anna might look great? That jacket is really nifty. I just don't love the horizontal folds on the dress. That's never my jam.
2011 in Chanel
This was "Alexander McQueen: Savage Beauty," and I'm sort of surprised Anna didn't wear McQueen as an homage. She may wish she had, as Karl saddled her with a ghastly Chanel that looks like a makeup palette they had to give away as a gift with purchase because it didn't sell. Meanwhile ALT is back there wishing he'd gone with the glitter robe instead.
2011 in Balenciaga
Mandatory Credit: Photo by Matt Baron/BEI/Shutterstock (1311021vl)
Bee Shaffer
Costume Institute Gala Benefit, Celebrating 'Alexander McQueen: Savage Beauty' at the Metropolitan Museum of Art, New York, America - 02 May 2011
She didn't go with McQueen EITHER. (This was right after Wills and Kate got married and I suspect Anna had a fleeting hope, once her dress designer was revealed, that Kate might attend or at least send along her dress. Neither happened.) This is not objectionable -- the colr is perfect on her -- but neither is it an homage to the kind of elaborate and evocative work that McQueen made famous. And if Anna isn't going to do it, you'd think Bee would be her vessel for getting with the theme.
2012 in Prada and Erdem
Mandatory Credit: Photo by Erik Pendzich/Shutterstock (1708508gc)
Anna Wintour and Bee Shaffer
Costume Institute Gala Benefit, Celebrating 'Schiaparelli and Prada : Impossible Conversations' at the Metropolitan Museum of Art, New York, America - 07 May 2012
For "Schiaparelli and Prada: Impossible Conversations," Anna DID break with Chanel and wear Miuccia's offering. It appears to be bedecked with a gold lobster, which, if that's the case, is a very Schiaparelli whimsical touch and actually makes this right on-point. It is the impossible conversation made possible. Well done, Anna. Bee is in a lovely Erdem that resists all of Erdem's worst flourishes.
2012
Mandatory Credit: Photo by Michael Bowles/Shutterstock (1708517el)
Anna Wintour
Costume Institute Gala Benefit, celebrating 'Schiaparelli and Prada: Impossible Conversations', Metropolitan Museum of Art, New York, America - 07 May 2012
This photo made me laugh. She's obviously posing this way for the photogs in front of her, and not because she's trying to give the ones behind her a show, but it's a behind-the-scenes moment that I liked.
2013 in Chanel for "Punk: Chaos to Couture"
NEW YORK, NY - MAY 06: Conde Nast Artistic Director Anna Wintour attends the Costume Institute Gala for the "PUNK: Chaos to Couture" exhibition at the Metropolitan Museum of Art on May 6, 2013 in New York City. (Photo by Dimitrios Kambouris/Getty Images)
Gorgeous, and not at all punk.
2013 in Dior
Mandatory Credit: Photo by Broadimage/Shutterstock (2320861p)
Bee Shaffer
Costume Institute Gala Benefit celebrating the Punk: Chaos To Couture exhibition, Metropolitan Museum of Art, New York, America - 06 May 2013
WEARING CHRISTIAN DIOR
Ditto. Although actually I'm not sure I think this is gorgous. It's got a lot of fiddly bits that look like bad depictions of constellations.
2014 for "Charles James: Beyond Fashion"
NEW YORK, NY - MAY 05: Anna Wintour attends the "Charles James: Beyond Fashion" Costume Institute Gala at the Metropolitan Museum of Art on May 5, 2014 in New York City. (Photo by Dimitrios Kambouris/Getty Images)
This looks like a mosaic of crumpled tissue paper.
2014 in McQueen
NEW YORK, NY - MAY 05: Bee Shaffer attends the "Charles James: Beyond Fashion" Costume Institute Gala at the Metropolitan Museum of Art on May 5, 2014 in New York City. (Photo by Dimitrios Kambouris/Getty Images)
Bee's poor dress is vomiting its lunch. Although that sort of volume and play on shape is, I think, a Charles James touch that makes it on-theme? I think? I am not great at the themes, y'all.
2015 in Chanel and McQueen
For "China: Through the Looking Glass," Anna wore a Chanel dress depicting... poppies, the source of opium. I am not sure I would have done that. (It also has echoes of Julianne Moore's custom dress in which she won an Oscar; I'm not sure I would have worn THAT either much less -- in Karl's shoes -- offered Anna anything that resembled an already-worn gown.) Bee's is a little awkward in the bodice area...
2015
... but divine from the back, and the color is once again magic on her.
2015
Anna's was complicated.
2016 in Chanel and McQueen
52042163 Celebrities at the MET Costume Institute Gala 2016 at The Metropolitan Museum Of Art in New York City, New York on May 2, 2016. Celebrities at the MET Costume Institute Gala 2016 at The Metropolitan Museum Of Art in New York City, New York on May 2, 2016. Pictured: Anna Wintour, Bee Shaffer FameFlynet, Inc - Beverly Hills, CA, USA - +1 (310) 505-9876 RESTRICTIONS APPLY: USA ONLY
The Manus x Machina theme didn't necessarily lend itself to a lot of obvious interpretations -- many of them were revealed later. This year and the one preceding were the first times I really wished people would arrive with pamphlets in tow. Bee looks cool, but as if she would be a better fit another year, and Anna has on a lot of fringe.
2016
Mandatory Credit: Photo by Andrew H Walker/Shutterstock (5669035h)
Anna Wintour
The Metropolitan Museum of Art's COSTUME INSTITUTE Benefit Celebrating the Opening of Manus x Machina: Fashion in an Age of Technology, Arrivals, The Metropolitan Museum of Art, NYC, New York, America - 02 May 2016
WEARING CHANEL
A LOT. It works, but I might have restricted it to JUST the shoulders.
2017, for "Rei Kawakubo/Comme des Garcons: Art Of The In-Between"
NEW YORK, NY - MAY 01: Anna Wintour attends the "Rei Kawakubo/Comme des Garcons: Art Of The In-Between" Costume Institute Gala at Metropolitan Museum of Art on May 1, 2017 in New York City. (Photo by Neilson Barnard/Getty Images)
This Chanel is certainly in-between SOMETHING. It looks like her party dress mated with a very furry dog.
Bee in McQueen
NEW YORK, NY - MAY 01: Bee Shaffer attends the "Rei Kawakubo/Comme des Garcons: Art Of The In-Between" Costume Institute Gala at Metropolitan Museum of Art on May 1, 2017 in New York City. (Photo by Dia Dipasupil/Getty Images For Entertainment Weekly)
This is her third consecutive year in McQueen (after NOT wearing it for the McQueen gala), and it's another very pretty one. She's good with a long train.
2018
Mandatory Credit: Photo by Andrew H. Walker/REX/Shutterstock (9662977kt)
Anna Wintour and Bee Shaffer
The Metropolitan Museum of Art's Costume Institute Benefit celebrating the opening of Heavenly Bodies: Fashion and the Catholic Imagination, Arrivals, New York, USA - 07 May 2018
Anna actually appears to have giggled in the direction of the "Fashion and the Catholic Imagination" theme, and Bee, in Valentino, is like, "Oh, screw it, I'll just be Sexy Devil."
2019
Mandatory Credit: Photo by Matt Baron/REX/Shutterstock (10225578q)
Anna Wintour
Costume Institute Benefit celebrating the opening of Camp: Notes on Fashion, Arrivals, The Metropolitan Museum of Art, New York, USA - 06 May 2019
And finally, "Notes on Camp." Anna cited a Susan Sontag quote: "Camp is a woman walking around in a dress made of 3 million feathers." Mission accomplished. It's also quite GOOD on her, and sh seems very light and happy.
2019 in McQueen
USA Rights Only - New York, USA -20190506- Metropolitan Museum of Art Costume Institute Benefit Gala 2019 -PICTURED: Bee Shaffer Carrozzini
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Back to her recent fav for this. It's a pantsuit, and the giant rosette and train. I don't know if it's campy, exactly -- this theme is open to SO much interpretation, and also was one that was ripe for accusation of not truly understanding it; I found it a real challenge to analyze -- but it WAS visually stunning and effective, crisp in a way she usually isn't while still maintaining the big ballgown elements she loves.