A Wintour’s Tale
This article is from the archive of The New York Sun before the launch of its new website in 2022. The Sun has neither altered nor updated such articles but will seek to correct any errors, mis-categorizations or other problems introduced during transfer.

Anna Wintour’s surname sounds like “winter.” A reader of Jerry Oppenheimer’s tell-all biography of the Vogue editor practically expects him to drag this coincidence out as hard evidence of her famously crisp demeanor. In “Front Row: Anna Wintour: The Cool Life and Hot Times of Vogue’s Editor in Chief,” Mr. Oppenheimer is clearly more interested in scribbling a caricature than in painting a portrait.
The prologue opens with an anecdote supplied by an unsuccessful job candidate for a features editor position at Vogue. Her name is not disclosed. She seems convinced that arriving on a winter’s day wearing open-toed stilettos without stockings and getting to her appointment on time (because “Anna fumes when she’s made to wait”) should guarantee her the “six-figure-a-year-with-perks” job. After a 20-minute interview with Ms. Wintour, the candidate is dismissed.
What does she take away from her rare tete-a-tete with one of the most powerful women in a multibillion-dollar industry? “A lot of people around Anna, and this is true at every fashion magazine, are gay men, and they’re the only ones at Vogue who are not terrorized by her. The thing is, she doesn’t really like women, which is certainly curious for the editor of the world’s most influential fashion magazine for women.”
Perhaps at this point, Mr. Oppenheimer ought to have tucked another idiom into his cliche-ridden prose: Consider the source. Such bitter stories provided by those rejected by Ms. Wintour at various times during her climb to the top make up the bulk of the text. A fixation on insignificant details obscures other big-picture themes that could genuinely illuminate how this woman works and who she is.
Though such fellow editors as Polly Mellen, Grace Mirabella, Liz Tilberis, and Grace Coddington provide some insights, telling comments from people who understand the reasons behind Ms. Wintour’s demanding behavior and standards of excellence are far between. For all the talk of staff turnover, lots of names recur year after year in the book.
Liz Tiberis, who seems to complain and rant the loudest, was promoted twice at Vogue in London under Ms. Wintour, and she recommended Ms. Tilberis to succeed her as editor in chief. And the dish of Toby Young, who penned “How to Lose Friends and Alienate People” after a brief stint at Vanity Fair, and Vogue editorial assistant Lauren Weisberger, who wrote “The Devil Wears Prada,” is familiar to anyone who ever read a review of either book.
In fact, it’s unsurprising certain sources cited did not last, given their apparent lack of dedication to their chosen profession. One, described only as a “staffer who quit in disgust,” says, “I mean, Vogue’s just a fashion magazine, a catalog to sell clothes, for God’s sake.” Heresy.
Drusilla Beyfus Shulman (whose daughter, Alexandra, is the current editor in chief of Vogue’s British edition) says of Ms. Wintour: “She was just all so terrific within that narrow compass of fashion. One might ask, is it worth feeling like that about a fashion magazine? And who cares, since it’s just selling advertising, really.” Ms. Shulman was fired from her staff position at Vogue’s British edition soon after Ms. Wintour took its reigns. Is it any wonder?
Mr. Oppenheimer’s tale beings at the very beginning, with the words,”Born on November 3, 1949.” In painstaking detail, Ms. Wintour’s upbringing is recorded, from the backgrounds of her parents – Bostonian Eleanor “Nonie” and Evening Standard editor Charles Wintour – to the tragic death of her older brother Gerald, who was hit by a car at age 10 while bicycling.
Descriptions of Ms. Wintour’s high school years at the all-girls North London Collegiate can be rather entertaining in their ordinariness. After mentioning that as a 14-year-old she would chatter about the older women who taught her, Mr. Oppenheimer brashly states, “Anna had already developed a thing about age and would later use is as both a creative tool and a weapon when she became a fashion editor.”
When she hid out in the bathroom to avoid gym class, he writes, “Manolo Blahnik was years away from designing ‘Sex and the City’ shoes, but somehow adolescent Anna foresaw that one day her legs would be a part of her signature look, so they needed to be slender and shapely, not thick and muscled.” Hiking up the skirt of her school uniform or ditching the mandatory beret are offered up as early indicators of her fashion forwardness.
Ms. Wintour never graduated from high school, nor did she pursue any higher education – an intriguing fact about a hardworking and intelligent woman whose parents met while both were studying at Cambridge University, but one that gets only cursory treatment in “Front Row.” Meanwhile, the author dwells on inconsequential items such as that, as a 26-year-old junior staff member, she spent nine months on the masthead at Harper’s Bazaar. Yet she said in later interviews that she spent a year there. For shame.
A brief allusion to an instance where her education was perhaps an issue arises during a retelling of the supposed rivalry between her and Tina Brown while the latter edited Vanity Fair: “Embarrassed by her lack of a formal education, Anna was envious of Brown’s, who had been a proper and serious student, and graduated from Oxford’s St. Anne’s College.” It would have behooved Mr. Oppenheimer to delve deeper into this weakness of Ms. Wintour’s and its implications. Some former employees mention that her strengths are mostly visual rather than editorial. And anyone who has been reading Vogue for years would notice that it has published less and less substantial editorial content – leading a trend picked up by other magazines.
In fact, the first time that the results of Ms. Wintour’s work (rather than her methods of achieving them) are questioned comes 250 pages into “Front Row” and 20 years into her career in fashion. When she was editor in chief of Vogue in London, certain editors wondered whether the eccentricity and quirkiness that had been a hallmark was fading away and being replaced with generic fashion spreads. Her next position, at House & Garden (renamed HG under Ms. Wintour’s editorship), brought more questionable decisions. Since that job is presented as a stepping-stone to American Vogue, however (which it likely was), her poor choices are of little consequence to the book or her career.
Yet those who pick up “Front Row” for juicy gossip will also be disappointed. Regarding a notorious tryst with reggae superstar Bob Marley, a “friend” of hers, Alida Morgan, says, “She says she didn’t have an affair, but she had this revelation and felt she had a mystical experience.” First boyfriends such as Piers Paul Read have nothing lurid to add: “Nothing irrevocable happened between us. I was young and inexperienced. We held hands, kissed occasionally.” During London’s swinging 1960s, Ms. Wintour is described as sipping Coca-Cola at popular clubs.
Ms. Wintour’s children seem to have been as well-behaved as she was as a teenager, and she comes across as a decent mother and her ex-husband, psychiatrist Dr. David Shaffer, as a devoted father. “Anna and Shaffer were also concerned and loving parents, and would do anything in the world for their children, Charlie and Bee. They were active as much as they could be in their fancy private schools.” The couple dutifully attended their parent-teacher conferences and Dr. Shaffer even volunteered to be a crossing guard, apparently. Nor is the breakup of Ms. Wintour’s marriage after 14 years over her relationship with Texan John Shelby Bryan particularly salacious.
Worst, for the kind of fashion-obsessed readers that Mr.Oppenheimer wants to attract, there are too few descriptions of Ms. Wintour’s clothes. Mr. Oppenheimer drops the rumor that she wears dark glasses constantly in order to protect delicate eyesight. But he himself is not one with an eye for style, despite his overuse of the word “fashionista.”
From the simple T-shirts that she favors in her 20s to the skirts of the Chanel suits that she puts on to trot to Conde Nast every morning at 8 a.m., her clothing is all described as “tight.” “Anna also sported another glamorous look – a chic and expensive outfit consisting of tight white T-shirts over Yves St. Laurent peasant skirts and leather boots,” he writes at one point, “all of which made her look like a skinny Cossack.”
Ms. Wintour may be unpleasant, but nothing in “Front Row” seems out of the ordinary for a driven businesswoman – particularly one in the business of fashion. As another unnamed source notes in “Front Row,” “When it involves Anna, it’s a bitch-eat-bitch world.”
DRAMATIS PERSONAE
Jerry Oppenheimer author of “Front Row ” has a way with descriptions. Here’s his take on the cast of characters in Ms. Wintour’s circle.
VOGUE
Tina Brown, Tatler/Vanity Fair/ New Yorker/Talk editor
“Brown had no problem with writing and, as was said later, took to magazine editing ‘like a deb to a canape.’ But while Brown was blond, tiny, buxom, and five years younger, she was no seductive glamour puss like Anna, and that caused her to be jealous.”
Diana Vreeland, Editor in chief
“‘Daring’ in an ‘artificial’ way” and “all flamboyance”
Grace Mirabella, Editor in chief and Mirabella founder
“A Jersey girl who had worked her way up through the ranks under Diana Vreeland.”
Grace Coddington, Vogue creative director
“She was a fashionista big-time, who could go from flaming red hair to dyed punk color at the blink of a perfect eyelash.”
Polly Mellen, Fashion editor
“A fashionista of the first order” who “had a reputation as a perfectionist, was difficult to work for, lived for fashion, and possessed a keen eye and astute taste.” Isabella Blow, Vogue editorial assistant (now stylist) “A busty, beet-red-lipped, micro-miniskirted eccentric Brit with a braying laugh who was sort of well-connected back in Mother England.”
Lauren Weisberger, Editorial assistant; author of “The Devil Wears Prada”
“A tall cute, preppy blonde just out of college who wanted to be a writer – a perfect Vogue specimen, or so she seemed.”
Andre Leon Talley, Editor at large
His “presence came a shock to [Ms. Wintour’s] subordinates because of his flamboyant manner and dress: patent leather pumps, striped stretch pants, red snakeskin backpacks, faux-fur muffs all superimposed on this gentle black giant who, in another world, could have been playing for the New York Knicks with his six-foot-seven frame.”
NEW YORK MAGAZINE
Ed Kosner, Editor in chief
“The married Ed Kosner was enthralled, if not infatuated, from the moment he laid eyes on her, and he gave [managing editor] Jones the green light to hire her at a salary that was said to be in the fifty thousand dollar range, the most Anna ever made.” According to an unnamed New York editor, “Ed had shiksa love, we’re talking majorshiksa love, full breakdown time.”
Laurie Jones, Managing editor
“A native of the small Texas town of Kerrville, a onetime cheerleader, superb athlete, former Miss Kerr County, and member of an exclusive WASP college sorority, Jones was stylish and immaculate, and would marry into a blue-blooded family.”
Karen Mullarkey, Photo editor “A six-foot-tall cowgirl type who possessed major clout and had a great reputation in the photography world; she was a protege of the noted photographer Oliviero Toscani.”
VIVA
Bob Guccione, Penthouse magazine owner
On his townhouse on East 67th Street: “The Guccione place eclipsed Hugh Hefner’s pad for sheer elegance and kitsch: A piano that once belonged to Judy Garland, a statue of a female saint, and two lead sphinxes with the head of Marie Antoinette were just part of the bizarre picture.”
Kathy Keeton, Guiccione girlfriend; headed Viva, where Ms. Wintour was a fashion editor at age 27
“She may have been a scantily clad dancer when Guccione first set eyes on her in the Pigalle club, in London’s Soho district when she was twenty-six, but she was a scantily clad dancer who read the Financial Times and played the market.”
HARPER’S BAZAAR
Liz Tilberis, British Vogue editor; later Harper’s Bazaar editor
“Power hungry in her own right”
PERSONAL LIFE
Jon Bradshaw, Writer; Ms. Wintour’s boyfriend “A devilish rogue with enormous appetites: of liquor, Johnny Walker Black being his favorite, but anything would do as long as someone else was picking up the tab; of recreational highs – a toke here, a snort there; of nicotine – at least three packs of unfiltered British Rothmans a day; and of rich foods.”
David Schaffer, Child psychiatrist;
Ms. Wintour’s husband Referred to as E.T. in a gossip column: “The snarky comment was in reference to the extraterrestrial of movie fame, who some apparently thought the distinguished psychiatrist resembled because of his large bald pate and big eyes.”
John Shelby Bryan, Texas businessman;
Ms. Wintour’s boyfriend “Along with being a macho jock, with a good business head on his broad shoulders, Bryan was a ‘mama’s boy,’ says another Houstonian – and that might have something to do with why he fell for Anna, and she for him.” An unnamed source described him as “the Marlboro Man to David’s Pillsbury Doughboy.”