Portrait of a Fashion Diva as Human Being

Due to an error at our printers, a portion of this article did not appear in the Jewish Journal print edition. The full article appears below.

In “The September Issue,” R.J. Cutler’s new documentary about the behind-the-scenes workings of American Vogue magazine, the formidable editor-in-chief Anna Wintour lives up to her reputation as the frosty doyenne of the fashion industry — aka Nuclear Wintour — who inspired Meryl Streep’s imperious performance in the film version of “The Devil Wears Prada.” 

As cameras capture the creation of the September 2007 issue, traditionally the largest edition of the fashion year, the diminutive Wintour intimidates designers and employees alike with her terse speech and icy glare. She unabashedly tells Oscar de la Renta he should reinterpret parts of his collection, and her critical remarks so fluster the head designer at Yves Saint Laurent that he vows to rethink his work. In one photograph, she decrees, the slender actress Jennifer Garner “looks pregnant”; in the issue’s cover photo, the actress Sienna Miller is too “toothy” and her picture must be retouched. When a Vogue staffer wonders aloud whether Anna would approve of a particular jacket, he quickly corrects himself, explaining that the garment is black (apparently a Wintour no-no): “I could get fired for that.” 

Yet the ruling diva, who often appears distant in her trademark sunglasses and severe bob haircut, nevertheless radiates a surprising vulnerability when she removes her glasses to reveal large green eyes in an on-camera interview. It becomes clear that despite her accomplishments, she still seeks validation from her relatives, who apparently regard fashion as trivial.

One of her siblings holds a prominent position in the field of low-income housing; another is the political editor of The Guardian; the third is a human-rights activist. “They’re brilliant,” the 59-year-old Wintour says. “My two brothers and sister are very amused by what I do — they’re amused,” she adds, in an almost self-deprecating tone.

Then there is Wintour’s college-age daughter, Bee, who explains that while she respects her mother, who wishes she would become an editor, she would prefer to become an attorney. Bee adds that she does not understand those who make fashion the center of their universe: “I would never want to take it too seriously.”

Cutler, a 47-year-old veteran filmmaker, grew up in a Jewish home in Great Neck, N.Y., and he identifies in an unexpected way with Wintour’s struggle between her public and private personas. “It’s like a classic Jewish folk tale, the story of Anna Wintour and her family,” he said of the editor. “It’s just so Jewish that this is a woman people bow down to everywhere she goes — they worship her, they’re terrified of her, they revere her. But the one group of people she wants to take her seriously — her family — think she’s silly.”

Cutler glimpsed Wintour’s vulnerability regarding her family in his very first meeting with the fashion monarch. The filmmaker finally secured an appointment with the often-inaccessible Wintour in October 2005, and reportedly even got himself a manicure for the occasion. He explained his documentary approach, which is observational rather than judgmental, inspired by his days working with the great cinema verité artist D.A. Pennebaker on films such as “The War Room.”

Anna Wintour, editor of American Vogue in
“The September Issue.”
Photo courtesy of Roadside Attractions

Wintour proved a “crafty negotiator,” he said, but was amenable to a movie because she had always hoped to structure a film around the creation of the all-important September issue. Cutler agreed to make that his focus, with one caveat: He alone would determine the final cut of the documentary, without compromise. Wintour said she understood this journalistic prerogative, because her late father had been editor of London’s Evening Standard. “I was really struck by the way in which she talked about her father,” Cutler recalled. “I thought, ‘This is Anna Wintour, she doesn’t know me from Adam, so why is she telling me about her father?’ That was the moment I really wanted to make the movie.”

So in 2007, Cutler and his crew captured Wintour and her entourage of designers, models, photographers and editors as they prepared what promised to be the fattest September issue ever. He followed the action during New York’s fashion week, filmed within the hallowed halls of Vogue, which are lined with couture, and traveled for shoots and re-shoots to Paris and Milan. He also captured closed-door meetings and some staff meltdowns. 

Along the way, he discovered that the centerpiece of the film should be the relationship between Wintour and Grace Coddington, Vogue’s second-in-command — a 68-year-old former model with flaming red hair who doesn’t wear even a scrap of makeup. Coddington is widely regarded as the most brilliant stylist in the modern fashion business; she joined American Vogue the same day as her boss, and she is the only Vogue staffer unafraid to spar with Wintour. 

Initially, though, Coddington wanted no part of the documentary. She reportedly even threatened to quit over Wintour’s decision to allow cameras at Vogue, and she snapped at Cutler to get out of her way whenever he approached.

“Fashion people see cameras and think, ‘The enemy has landed,’” Cutler said. But after four months of hostility, Coddington relented upon viewing previous films by Cutler and his director of photography, Bob Richman. “My instinct was that Grace would connect to Bob’s artistic soul the way she had connected with so many photographers,” Cutler said.

“Anna and I understand each other,” Coddington says in the film. “She knows I’m stubborn; I know she’s stubborn. I know when to stop pushing her.” Coddington pauses, and then says dryly, “She doesn’t know when to stop pushing me.”

Cutler himself came across as both bold and opinionated in an interview at a Hollywood bistro; he fiercely defends Wintour against those who would indiscriminately label her with the b-word. Wintour is paid to nix ideas, he insists; she is too busy to mince words, and while she is demanding, she is also forthright, hardworking and passionate about her job.

“Now, I’m not naïve; fashion is a bitchy business,” Cutler added. But he said he thought a recent “60 Minutes” interview with Wintour went too far. “The subject of the whole damn thing was, ‘Are you a bitch or not?’” he said. “Besides the fact that that is sexist, it’s so boring. Morley Safer would never ask a man, ‘Are you an asshole?’ But he actually looked Anna in the eye and asked, ‘Are you a bitch?’ She should’ve given him the finger.”

As bold as he is with his opinions, Cutler laughed a tad sheepishly when asked about how his Jewish family reminds him of Wintour’s. He told a story of how his mother, during his senior year at Harvard University, was concerned when he announced his initial career plans, which included directing theater because he enjoyed the human drama explored onstage. His mother replied that if he liked human drama so much, how about exploring courtroom drama as an attorney? Or life saving on the operating table as a surgeon?

Cutler actually blushes when asked about Wintour’s response to his film. In the documentary, her scathing one-liners are at times amusing: “This type seems so large and pretentious — it looks like something for blind people,” she says on camera at one point. Did Wintour have any such critiques about “The September Issue?”

“She had about 30 of them,” Cutler said. “But you would want nothing less from Anna Wintour, wouldn’t you? You would want her to be opinionated, to be forceful.”

And, he added, she was true to her word. “She honored her agreement that this was my movie, and she has done a lot to support it. I say, ‘God bless her.’”

“The September Issue” opens Sept. 11.


Designer Fashions Hobby Into Business

When M.R.S President Molly Stern was growing up in Los
Angeles and attending Yeshiva University of Los Angeles High School, she felt
out of place. “I fancied myself a tomboy, if you will,” said the 30-year-old
designer of the M.R.S label. “And I never really felt comfortable with my body,
being a curvy, short woman in Los Angeles.”

In a city where most clothes are made to suit Los Angeles’
idea of the perfect female body type (tall and thin), Stern had difficulty
dressing herself in a way that reflected her artistic style and enhanced her
curvy body type.

“I have a high taste for fashion,” Stern said. “But I’m a
round, little, cute Jewish girl with size-C breasts and an hourglass figure,
and it is hard to find clothes that fit and are cute and comfortable, and that
don’t make you feel like, ‘Oh my God, I have to hold my stomach in,’ or ‘Oh my
God, my boobs are so big they are falling out of my shirt.'”

Stern, who is also a makeup artist catering to a celebrity
clientele, decided to take these sartorial matters into her own hands. When she
moved to New York in 1998, and found herself housebound during the harsh
winter, she decided that she needed a hobby.

“It was snowing, and I didn’t know what to do with that, so
I started to sew these sexy T-shirts,” she said. “They were sort of punk
inspired and had a deconstructionist feel to them — very sort of raw and
organic and were very conscious of flattering the body.”

After getting rave reviews about the T-shirts from her
friends, Stern took them to a downtown Manhattan store, where they were sold on
consignment. The T-shirts quickly sold out, and the store needed to order more.

In the meantime, Stern’s roommate, a celebrity fashion
stylist, asked Stern to make a shirt for actress Claire Danes, which Danes wore
in public. Stern also asked many of her actress makeup clients if they were
interested in garments that she made — and they were.

“Slowly but surely things like that started happening, which
gained a celebrity buzz,” said Stern, who called her label M.R.S, after her
initials (Molly Rebecca Stern). Today, M.R.S clothes are likely to be seen in
the fashion pages of Vogue and worn by celebrities such as Reese Witherspoon,
Milla Jovovich, Gisele Bundchen and Julianne Moore.

The philosophy behind the label is that women should feel
“modestly sexy,” an idea that Stern said was inspired by her religious

“I went to yeshiva myself, and I feel very aware of being
appropriate and being able to be in any sort of situation and feel good about
who I am and what I look like,” she said. “And that was always a struggle for
me within the community of being an artist and being more avant garde than the
average yeshiva girl, so I constantly had a struggle of feeling secure of this
is who I am and this is what I look like. [M.R.S clothes] were marrying the
concept of wanting to be accepted and appropriate and wanting to be unique and

In a an interview with Nylon magazine, Stern described her
personal clothing style as “lady and the tramp,” and, to some extent, M.R.S
clothes ascribe to the same philosophy. Simple T-shirt jerseys are gussied up
with ruched bustlines, held together with small strings of beads and sequins.
Many of the seams are hand-sewn, with overlocking stitches on the outside of
the garment, with asymmetrically cut hems, sleeves and necklines that create
the kind of disheveled look that would be welcomed at a Paris fashion show.

M.R.S had its debut fashion show last spring at Barneys New
York, and The New York Times called the clothes “a delight.” Stern found
herself inundated with orders — more than 1,000 pieces were ordered from the
collection — meaning that Stern and her small team of six workers in Brooklyn
had to work overtime to fill them.

Although M.R.S clothes are expensive (prices start at $60
for undershirts and go up to $5,000 for the couture dresses), there is such
high demand for them, that Stern is now looking for investors to help her
expand the company.

“I don’t know one woman who hasn’t at some point in her life
spat at herself in the mirror because she didn’t like the way she looks,” Stern
said. “My mission is to make that not happen anymore.”

“If you feel good in your clothes, you can do anything,” she
continued. “If we can inspire a nation to feel satisfied and exude their unique
sensuality or sexuality without it being obvious, then I think it is a really
exciting idea.”

M.R.S clothes are available at Barneys and Ron Herman
(formally Fred Segal) in Los Angeles.