1. April 1992: Anna praises Anita Hill.
Anna in a 1992 photo most excellently captioned: “Vogue’s always-warm-and-jolly editor, Anna Wintour, from the neck up the most stylish woman in America.”
Following Hill’s allegations that Supreme Court nominee Clarence Thomas sexually harrassed her, Anna told a Los Angeles Times reporter writing about the influence of gender roles on the current fashion season, “Anita Hill made women feel pride in being women.” The runways were moving away from mannish 80s power suits, and as you can see, Anna was embracing this trend, evidently feeling pride in a lamé turtleneck, possibly worn bra-less.
3. July 1992: Attends “NY Is Fashion” event in Central Park.
Believe it or not, this is not a recent Instagram of a hipster pointing to a taco truck — it’s early 90s Anna!
Designers like Anna Sui and Todd Oldham showed fall collections to visiting Democratic Delegates. Hillary Clinton, “the most hoped-for presence,” didn’t show. When Newsday asked her what the event might achieve, she replied, “Maybe it’ll help the delegates with their wardrobes a bit.”
5. January 1993: Anna MIGHT have begun plotting how to make over Hillary Clinton.
So as you can imagine everyone thought Hillary was the PINNACLE of style in this. No, not really — Hillary’s inauguration outfits were panned. The New York Times called her daytime hat a “blue unidentified flying object.” And Newsday reported: “About the worst anyone would say about Hillary’s gown — the violet sheath with leaf-patterned lace and a blue-violet chiffon overskirt by New York designer Sarah Phillips — was ‘well, it’s not my taste,’ which is a rave, when you consider how catty fashion people can be.” (The designers Clinton wore at the time reported heightened sales, not unlike that of Michelle Obama’s favorite clothes-makers today — too bad the ones the Vogue set disapproved of didn’t last long.) The paper added that “a prominent fashion editor is said to have beseeched a very well-known designer to redress the first lady, saying ‘Donna, you’ve got to do it for the country.’” Now… WHO might that be?
8. February 1993: Anna Wintour wrote to Hillary Clinton, offering her style advice.
Despite Anna’s braless-lamé-and-turquoise-suede and oversized-sweatshirt-with-another-sweater-tied-around-her-waist looks, she felt she had something (shiny?) to offer Hillary. Vogue’s publicist at the time, Paul Wilmot, told the New York Times for a story that ran February 7, 1993: “This was just a way to offer informal assistance.” He continued, “We read that she was getting barraged from designers sending in sketches and people calling. We ourselves were getting called daily about what she was wearing and what our opinion was. We simply offered to sift through all of the fashion for her.” The Times didn’t find the offer out of the question, noting that British Vogue offered advice to Princess Diana on her wardrobe in the Eighties.
10. February, 1993: Hillary dresses well (read: kind of trendy!) at her first major White House event prompting questions of whether Anna helped her.
A photo of Hillary wearing Donna Karan’s famous cold shoulder dress (sent to her by Karan, paid for by the First Lady, the New York Times reported) at the Governors’ Ball at the White House appeared on the front page of the paper wearing Donna Karan’s famous cold shoulder dress. The dress was met with the opposite reaction of her disastrous inauguration wardrobe. Was this Anna’s influence or was Hillary trying to show off her hot delts?
She did not land the cover (which went to Sharon Stone, whose visage was allowed at this time to display smile crinkles), but she appeared inside the magazine wearing Donna Karan again. Bill Clinton apparently made a cameo during her photo shoot with Annie Leibovitz and remarked, “You’re all dressed up like a Christmas tree.” Hillary, who listened to Barbara Streisand to loosen up for the shoot (compare that to Michelle Obama’s musical tastes) refused to wear the black velvet evening gown off-the-shoulder, as it was intended. Hillary yanked the dress down to show Bill how it was supposed to be worn, exclaiming, “They wanted me to wear it like this.”
14. September 1994: Anna joined fashion industry bigwigs at the White House for a breast cancer charity event, hosted by Hillary.
Claudia Schiffer in a 1994 Fashion Targets Breast Cancer campaign.
Ralph Lauren, Oscar de la Renta, Louis Dell’Olio and Donna Karan joined her to help kick off a fundraising initiative sponsored by the Council of Fashion Designers of America. The project included selling limited edition white tee-shirts with a bull’s eye graphic and the words “Fashion Targets Breast Cancer” for $15 in stores around the country. So, just the kind of tee-shirt launch that needs a White House party, in other words.
16. September 1996: Anna hosts a breast cancer charity breakfast at the White House with Hillary Clinton and Princess Diana.
The reports pretty unanimously agreed that Diana — who had just gotten divorced the previous month — overshadowed Hillary, which she did to everyone before, during, and after her divorce, to be fair. Anna must have been overjoyed to be ensconced on stage with two of the most famous women in the world, and Ralph Lauren, who managed to wear the biggest shoulder pads of all.
18. FUN BONUS PHOTO OF DIANA AND ANNA HANGING OUT! GALA-ING!
Hillary didn’t go to the evening Gala for this breast cancer thing but this pre-Instagram Instagram is just too good not to share!
20. December 1998: Hillary Clinton is the first First Lady to cover “Vogue.”
In the wake of the Monica Lewinsky scandal, Hillary had a glamazon moment on the cover of Vogue “She’s come out of a disgusting situation, frankly, with incredible grace,” Anna said of the cover, according to a November 24,1998 edition of USA Today. “She behaved with intelligence and dignity. We felt, in a way, she was our woman of the year.”
After the affair, Hillary’s approval ratings soared to over 60 percent. This probably helped explain why her spokeswoman at the time, Marsha Berry, didn’t feel the need to justify the sitting, aside from saying she wanted to promote the White House Millennium Council’s efforts to highlight American heritage and culture, which the accompanying article addressed.
Anna discussed the issue on CNN, emphasizing how much Hillary enjoyed her photo shoot, how triumphant a moment it was for her — and how good she looked! “I think she’s feeling very good about the way she looks,” Anna said. “And I think, to all women, being on the cover of Vogue goes beyond power and politics. And it was almost a sort of, you know, sort of triumphant statement, I feel, on her part.” She added that the photo of Hillary on a White House balcony wearing a white Ralph Lauren shirt was the then-first lady’s favorite.
25. July 1999: News breaks that Anna will leave her husband, Dr. David Shaffer, for Telecommunications tycoon J. Shelby Bryan.
Shelby Bryan (left) with Anna Wintour and Jan Wenner at a Zac Posen fashion show in February of 2003.
Shelby, a billionaire, was described in reports of his and Anna’s divorces as a friend of and fundraiser for Bill Clinton. If Anna and Dr. Shaffer were a Power Bar, Anna and Shelby were like one of those scary muscle bars containing 50 grams of protein or whatever it is they sell now.
27. October 1999: The Clintons host a reception for “Vogue” photographer Annie Leibovitz at the White House, attended by Anna.
They were celebrating Leibovitz’s photography show and new book. There was a charity tie-in. The usual “powerful people get together to pose for photos and make people talk about them” sort of event.
29. October 1999: Anna’s new boyfriend lands a political appointment.
The Washingtonian reported in an article dated November 3, 1999 that as news of Wintour and Shelby’s divorces dominated tabloid headlines in New York, papers in Washington were reporting that President Clinton was in the process of adding Bryan to his Foreign Intelligence Advisory Board. “White House chief personnel director Bob J. Nash wanted to delay the appointment, but Bryan wouldn’t hear of it,” the publication reported. “The Texas-born Bryan has raised millions — and contributed an estimated $500,000 to the Democratic Party — so the White House caved.” Whatever, Clinton’s term was almost over anyway.
During the Bush years, “Vogue” highlighted a number of political figures, like First Lady Laura Bush, who had a well-publicized love affair with exorbitantly expensive clothes by Oscar de la Renta. But she wasn’t special enough to shoo Gisele and her breasty backpack carrying off the cover.
In the coming years, bipartisan political coverage continued in Vogue’s pages.
34. December 2003: Hillary Clinton appears in “Vogue” again.
Hillary and Anna in 2003.
This time, Hillary sat for her portrait session as New York’s senator. All was merry in HillAnna land — but it wouldn’t last.
37. January 2005: First Lady Laura Bush appears in “Vogue.” Again.
38. August 2007: Hillary Clinton’s deputy chief of staff Huma Abedin appears in “Vogue.”
Are we seeing an “elbow out, look that way out the window” trend in the posing here yet?
40. November 2007: Hillary Clinton canceled a photo shoot for “Vogue” out of fear of looking “too feminine.”
Liz Smith broke the news in the New York Post that a big Hillary feature was off. Vogue issued a statement explaining, “We were told by Ms. Clinton’s camp that they were concerned if Clinton appeared in Vogue that she would appear too feminine.”
42. January 2008: Anna addresses Hillary’s “Vogue” snub in her editor’s letter.
“The notion that a contemporary woman must look mannish in order to be taken seriously as a seeker of power is frankly dismaying,” she wrote. “Margaret Thatcher may have looked terrific in a blue power suit, but that was 20 years ago. I do think Americans have moved on from the power-suit mentality, which served as a bridge for a generation of women to reach boardrooms filled with men.”
In June of that year, Paula Reed, who was supposed the write that story, told Women’s Wear Daily that Hillary’s communications director Howard Wolfson told her “We already have the women’s vote in the bag.” And: ‘We thought we were going to be in a bigger dogfight. We don’t need you anymore.” Reed said, “This was right before Iowa. What an idiot!”
No ballgown for YOU, Alaska lady.
46. June 2008: Anna hosts an Evening with Michelle Obama to raise money for the Obama campaign.
Michelle was just becoming a fashion icon (the pictured Isabel Toledo dress accessorized with a diamond dream catcher she wore that night was met with orgasmic approval from fashion people) when Anna chaired this event with her boyfriend Shelby Brian, Calvin Klein, and André Leon Talley. For $1,000 guests could get a photo with Michelle, and for $10,000, they could attend dinner with her at Klein’s house. All that money, and to think, probably no one ate.
48. July 2008: Anna lands on the list of people who raised $100,000 to $200,000 for Obama’s campaign.
One of the best fashion photographs of all time.
Vogue’s André Leon Talley joined her on the list. Cold stares all around.
50. November 2008: “Vogue” denies Anna will leave the magazine to work for Obama.
Rumor was she’d accept a “cultural post of some sort” in the White House. A rep for Vogue denied the rumor, saying Anna “won’t be working for Obama in any way.”
52. January 2009: Reports emerge that Anna will become an ambassador to France.
Anna receiving a French Legion of Honor medal from French President Nicolas Sarkozy in the summer of 2011.
“Page Six” reported at the time that “at least one person in the magazine industry” said this would be possible. See how these rumors get started?
54. March 2009: Michelle Obama appears on the cover of “Vogue.”
André Leon Talley wrote the cover story, in which he asked Michelle about the cardigan she wore the night Barack won the election that some people really hated. “I’m not going to pretend that I don’t care about it,” she told him. “But I also have to be very practical. In the end, someone will always not like what you wear — people just have different tastes. Some will think that a sweater was horrible, [but] I was cold; I needed that sweater!”
(Years later, I still find this cover a bit awkward.)
56. November 2009: Anna lands a spot on a White House Committee!
The Committee on the Arts and Humanities, which also includes, Sarah Jessica Parker, Forest Whitaker, Edward Norton, Yo-Yo Ma, and Teresa Heinz Kerry. Their task is to advise the president “on how to expand the role of arts in society,” Women’s Wear Daily reported.
As secretary of state, Anna finally got the Hillary story she wanted — and HillAnna was one again. In it, we learned that Hillary loves Mad Men, puts on her own makeup (“mascara, lipstick, blush, and a little powder”), and has drinks with reporters. You know, the really hard, gritty news stuff.
Guests like Harvey Weinstein, Georgina Chapman, and Donna Karan paid $30,400 to attend. Anna had extra air conditioners trucked into her home for the occasion.
In this TOTALLY RIVETING video of her arrival (with her boyfriend Shelby) reporters pepper her with extremely serious questions. She says she’s wearing Chanel (duh) and then one asks, “Who are you most interested in talking to tonight?” Anna replies, “The Chinese Premier.” (Duh, again — who else is she going there to talk to? Someone she knows already like Michelle?) The reporter counters, “What will you ask him?” And Anna says, “Will he invest some money in Chinese fashion?”
64. March 2011: “Vogue” profiles Syrian First Lady Asma al-Assad.
The 3,200-word story, by Joan Juliet Buck completely ignored the country’s atrocious human rights violations, describing Asma as “glamorous, young, and very chic–the freshest and most magnetic of first ladies.” Buck called her husband, President Bashar al-Assad, “a precise man who takes photographs and talks lovingly about his first computer.” The profile was met with such distaste (as expected) that it quickly disappeared from Vogue.com.
66. August 2011: Anna dines with Barack in Harvey Weinstein’s basement.
Guests like Alicia Keys, Jimmy Fallon, and Vera wang paid $35,800 to attend. Harvey and Barack gave little speeches As I wrote at the time, the two “shared a joke about how Weinstein had loaned him a rough cut of The King’s Speech on Martha’s Vineyard last year when the president asked if he could borrow a movie (which is like asking Anna Wintour to borrow a dress — who does that?). “
68. January 2012: Anna and the fashion industry announce “Runway to Win” to raise money for Obama.
71. April 2012: Buck addresses the controversial al-Assad profile.
She told NPR: “I think that Vogue is always on the lookout for good-looking first ladies because they’re a combination of power and beauty and elegance. That’s what Vogue is about. And here was this woman who had never given an interview, who was extremely thin and very well-dressed and therefore, qualified to be in Vogue. And they had – Vogue had been trying to get her for quite a long time.” So if she were fat the embarrassment for all involved would have been spared?
She discussed gay marriage and made a quip about the devil wearing Prada and there was much rejoicing.
75. June 2012: Anna finally discusses the outlandish Asma al-Assad profile.
Her statement: “Like many at that time, we were hopeful that the Assad regime would be open to a more progressive society. Subsequent to our interview, as the terrible events of the past year and a half unfolded in Syria, it became clear that its priorities and values were completely at odds with those of Vogue. The escalating atrocities in Syria are unconscionable and we deplore the actions of the Assad regime in the strongest possible terms.”
77. June 2012: Rumors about Anna getting a job as ambassador to London return.
No one can resist speculating about this again as Wintour’s fundraising efforts (she’s raised $500,000 for Obama’s reelection bid so far) continue to garner prime media coverage. But WAKE UP FASHION PEOPLE: That ill-fated Syrian First Lady profile mess just happened basically yesterday.
79. June 2012: Anna releases a video announcing contest for normal, not rich people to attend a fancy fundraising dinner.
Her cohost for this event was Sarah Jessica Parker. This was all very upsetting to Republicans.
Beck mocked her accent (Anna is British) and referenced The Devil Wears Prada, explaining to his viewers that Anna “was the devil part. She was the person who was actually in the movie treating her co-workers… like garbage, waiting on her every whim. She is what [Obama] says capitalists are like all the time. She is everything she says the Republicans are, and she’s an Obama supporter.” Witty, that one.
83. June 2012: Debuts Bark for Obama designer dog products.
At a Runway to Win event in Chicago, Anna announced a fun addition to the movement’s online store: designer doggie accessories! They include a $40 dog tee by Marc Jacobs. Thakoon also made a dog leash and collar for $45.
85. June 2012: Barack and Michelle attend another fundraiser hosted by Anna.
Obama’s motorcade leaving Sarah Jessica Parker’s house in New York City.
Sarah Jessica Parker co-hosted the event, attended by Michael Kors, Meryl Streep, and other luminaries. The lucky contest winner who got to go by making a small donation to the Obama campaign online was Robin Hunt, a health care professional from Baltimore who works at Johns Hopkins Hospital, and brought her mom Elvita with her (aw).
Michelle, who is so used to this nonsense, was not phased by the fanciness of the $40,000-a-ticket event or the many fashion people that would engulf her. She previously told the Insider: “I’m going to wear jeans and some flats.”
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