the times | Thursday April 28 2022 3times2
magazines, she edits people too
completely unsure, I’ll pretend I know
exactly what I’m talking about and
make a decision.”
This means her decisions are
inscrutable verging on inexplicable.
Wintour told David Letterman that
she gives people “very clear direction”,
but sometimes “unfortunately, they
don’t hear the answer that they would
like to hear”. She appears by turn both
bizarrely loyal and disloyal. In Anna,
Lisa Love, the former West Coast
director of Vogue, says, “If you get
frozen by her, that’s it... you’re done.”
In the same book the Malaysian
designer Zang Toi describes his delight
at being launched by Wintour, but
a few years later he was out. Wintour
saw Toi at an event, “looked at him
for two minutes, saying nothing”,
Odell writes, “and then walked off
with her bodyguard”.
Wintour made Talley the creative
director of Vogue in 1988, and the
highest-ranking black man in fashion
at the time. Their bond “was just
perfectly understood between us, like
a silent language”, as he wrote in his
memoir, The Chiffon Trenches. “So
much in fashion is unspoken.”
Talley augmented the ultra-
disciplined Wintour mythology, such
as her 5.45am rise to play tennis,
revealing that Wintour did not like a
meeting to go beyond eight minutes,
and often left restaurants before the
meal was even served, saying, “Let’s
go back to the office.” Or as Brown put
it of Wintour: “Clip clip clip,
progressing things without second
thought or self-doubt.”
But a couple of decades later Talley
was iced out of all his roles.
“She decimated me with this silent
treatment so many times; it is just the
way she resolves any issue,” Talley
wrote in the book. “Who is she? She
loves her two children... But so many
people who have worked for her have
suffered huge emotional scarring.”
“The last time I saw her in public,
I said hello to her and she turned her
back on me,” Talley told Women’s
Wear Daily in 2020; he died this year
aged 73.
Wintour’s family may have mocked
her in her early years for being
“deeply unserious”, but actually she
appears deeply serious. Humour is not
her style. Some people approach
fashion as giggly good fun. Never her:
style is substance, and her tenure is
marked by a shift from models with
nothing to say to politicians, singers
and actresses.
In 2020 she drew flak for an
awkward apology for lack of diversity
in Vogue. A few months later she
was made global chief content officer
for Condé Nast, an even more
powerful job, in her seventies, in a
business fixated on youth. Wintour
unapologetically supports the fur
industry: one trademark look is a
fur cape, full regal ermine. Mud
doesn’t stick.
At the Met Gala sometimes the
superstars find waiting in line to meet
an editor to be an unusual power shift.
One British journalist in 2006
witnessed Jennifer Lopez reach the top
of the steps and discover the long
queue to greet Wintour. “OK, what’s
happening?” Lopez said to the queue.
The celebrities stayed in line.when they come too close to
the subject of her two long-
term relationships with, first,
David Shaffer, a psychiatrist,
then Shelby Bryan, an
investment tycoon. Now she is
seen more often with her old
friend the actor Bill Nighy.
Moving alone to London
while heavily pregnant with the
first of her two children to edit
British Vogue, leaving Shaffer in
New York, was the last time she
publicly wondered at the cost of
her ambition. “The logistics are
terrible,” she said in that last
vulnerable interview in 1986.
“I wake up at night in a cold
sweat. Endlessly, parts of one
think, ‘I’m crazy. I should stay
home, look after my baby, have
a nice quiet life.’ ”
Since then her private life
has been behind a velvet rope.
The mystique is important;
show don’t tell, as both Queen
Elizabeths might attest. New
teachers are often told that
to smile weakens authority
— “don’t smile until
Christmas”, especially women,
who are expected to smile
more and as a result are
respected less. Wintour didn’t
smile much until she was 70.
The job of a leader, especially
in Manhattan, is not primarily
to be liked, and Wintour
challenges us to apply that
standard equally to male as
well as female bosses.
Tina Brown was Wintour’s
erstwhile close rival when they
were both British magazine
editors in New York. In her
diaries, The Vanity Fair
Chronicles, Brown describes
watching Wintour as Shaffer,
then her husband, gave a
funny after-dinner speech at
an event in 1989. Brown noted
Wintour’s face was “impassive” — “I
wonder what Anna herself thinks?”
Shulman said in her piece for Air
Mail that “Anna has always used
silence as a well-honed weapon.”
Shulman’s friend reported of going to a
nightclub with Wintour in London in
the 1980s that “Anna was going
through one of her silent phases and
just sat there”. Shulman expressed
surprise that Wintour was surrounded
by so many admiring men when she
contributed so little; her friend
retorted that the silence “fascinated”.
Shulman says Wintour bit her tongue
when others were promoted over her,
and “that ability to keep her counsel
has stood her in good stead in the
game of snakes and ladders of
corporate power.
“What is her opinion of... well,
actually, anything?”
Wintour makes decisions fast and
without soul-searching. RJ Cutler, who
filmed the 2009 documentary The
September Issue, said of her: “‘Yes, no,
yes, no,’ that’s Anna Wintour,”
although in a talk to Women’s Wear
Daily she revealed she sometimes
winged it.
“People respond well to those
that are sure of what they want,”
Wintour said. “What people hate
most is indecision. Even if I’mLeft: Anna Wintour,
the editor-in-chief of
Vogue, at the 2019
Met Gala in New York.
Above, from top:
with Bill Nighy in
2020; Beyoncé at the
2015 galaThis inarticulateness may seem
strange for a journalist, but then
Wintour is not a typical journalist:
whenever her mighty influence is
invoked it is not within the media but
as the kingpin of the entire fashion
industry. This is akin to the editor of
one political magazine calling the
shots on politics on both sides of the
Atlantic. She is rumoured to be worth
$35 million, a fraction of the money
she has generated for her employer. In
Odell’s book Wintour is tight-lipped
about retirement other than “telling
friends maybe she’ll do something
where she’s being paid for her advice
instead of giving it away for free”.
Her father, Charles, once told The
Sunday Times that when his daughter
made her ugly brown school skirt at
North London Collegiate into a mini,
the headmistress ripped down the
hemline. “Anna had to go home on the
Tube in a torn skirt,” Charles recalled.
“Quite seriously it finished her interest
in academic life.”
In an interview she gave to The
Guardian in 1986, the last to expose
any vulnerability, Wintour intimates
where her drive to succeed came from:
the humiliation of an intellectual
family making her feel “rather a
failure” before she had even begun.
“Most of the time I was hiding
behind my hair and I was paralyticallyshy,” Wintour said. “I’ve always been a
joke in my family. They’ve always
thought I am deeply unserious. My
sister would ring up and say, ‘Where is
Anna, is she at the hairdresser’s or the
dry cleaner’s?’ ”
What her family failed to
understand was the power of
neurodiversity. Wintour’s talent was
visual not verbal. In her mid-twenties
she cut off her long hair and created
the character “Anna Wintour”.
It doesn’t matter that in an industry
obsessed with the new, Wintour
is unchanging — for she is a brand,
not a fashion. It doesn’t matter that
she does not write much or care much
for writers.
Richard Story, a former staffer at
Vogue, told a previous biographer,
Jerry Oppenheimer, that Wintour
rarely if ever reads Vogue’s arts
coverage, but from the beginning at
Vogue demanded Polaroids before
photographers began any shoot.
Wintour’s belief in image would
only grow as the 21st century’s social
media unrolled.
And most of all it doesn’t matter
that she toggles between the shy
person’s directness and silence, when
its effect on others became so useful.
She gives short shrift to probing
interviewers, with phrases like “move
on” or “have you got enough?” usedCOVER AND BELOW: GETTY IMAGES‘I wake up
at night in
a cold
sweat,’ she
said in
- ‘I’m
crazy. I
should
have a nice
quiet life’