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Exclusive | Former fashion assistant at Vogue recalls Ann...
Angela Barbu · 2026-04-26 · via New York Post

Wintour knows how to throw shade.

A former fashion assistant at Vogue could hardly believe her eyes during her job interview with Anna Wintour — because throughout the entire sit-down, the icy editor-in-chief never once removed her specs.

“I remember walking into her office and she spun around in her swivel chair wearing sunglasses,” Jenny Syquia told The Post ahead of the May 1 premiere of “The Devil Wears Prada 2.”

Anna Wintour smiling while wearing a red plaid suit, sunglasses, and multiple necklaces.

Former Vogue fashion assistant Jenny Syquia told The Post that Anna Wintour never removed her sunglasses during her job interview. Ron Galella Collection via Getty Images

“Nobody had warned me she would be wearing sunglasses, so it really threw me off. It’s very disconcerting to talk to someone when you can’t see their eyes, because eye contact is such an important part of communication.”

The Binghamton, NY, native started working at the magazine in 1990 at its Midtown offices at 350 Madison Ave. — and quickly learned the do’s and don’ts when it came to elevator etiquette.

“I remember there being a rule in the building that if Anna Wintour was in the elevator, nobody else got in. Everyone just knew that,” she said.

Syquia, now 58, began as an editorial assistant and was then promoted to one of Wintour’s fashion editorial assistants — and recalled their ruthless leader’s “incredibly strong presence.”

“She was very quiet, very direct, and extremely sharp. She wasn’t warm and fuzzy — but she wasn’t mean either. She was simply very clear, very focused, and very much the boss,” she said.

Headshot of model Jenny Syquia former Vogue fashion assistant smiling.

Syquia, a native of Binghamton, landed the coveted role in 1990. Eric Josjö/WEI

One Valentine’s Day, when Syquia’s boyfriend sent 1,000 roses to her office, Wintour showed her playful side by popping her head in and asking, ‘What’s going on in here?'” she recalled.

“My direct boss explained … and Anna reacted with a very amused, ‘Wow!’ It was a very funny moment and I have to say she honestly looked pretty impressed.”

Syquia never wanted to work at Vogue.

Upon graduation from Boston University, where she double majored in English and international relations, she moved to Manhattan with hopes of becoming a writer at Vanity Fair.

However, a human resources rep at Condé Nast, which owns both glossies, decided she was better suited for their fashion magazine.

“When you walk in there, they typecast you. And I went into HR and she just said, ‘You belong at Vogue.’ I had zero interest in fashion,” recalled Syquia, a former model, who now runs a jewelry brand, TRIT.

Jenny Syquia working at Vogue, on the phone at her desk.

“There were no computers, and I just had these lists of phone numbers. When we ‘called in’ a look, it meant contacting the brand, booking the pieces for a specific date, sending a messenger to pick them up,” she explained. Courtesy of Jenny Syquia

Her role at Vogue, which paid a starting salary of $3.85 an hour, entailed coordinating all the fashion that appeared in the magazine, and its photoshoots.

“You were also responsible for waking the models up in the morning, coordinating transportation, arranging permits for shooting locations, organizing catering — essentially managing the entire logistics operation,” she said.

“If anything went wrong on a shoot, everyone looked at the fashion assistant.”

Madonna on the cover of Vogue magazine in a purple cap and a striped shirt with brown studded pants.

Syquia stood in as the fit model for Madonna when she was on the cover of Vogue in 1992. Vogue

When Madonna graced the magazine’s October 1992 cover, Syquia stood in as her fit model.

“Instead of wasting Madonna’s time, when all the clothes would come in, before they would bring the racks in for Anna Wintour to say ‘yes’ or ‘no’ to, they would have me try them on, because I’m 5′ 3” and was 34-24-34, the exact same as Madonna,” she said.

“I remember specifically trying on the pants she wore in that cover image. They were actually a little long. You can see it in the photograph, and I remember noticing it during the fitting.”

Anne Hathaway, Meryl Streep, and Stanley Tucci in "THE DEVIL WEARS PRADA 2"

In “The Devil Wears Prada” films, Miranda Priestly, played by Meryl Streep, is based on Wintour. Walt Disney Co./Courtesy Everett Collection

Syquia, who was a college classmate of Carolyn Bessette Kennedy, would run into her at Calvin Klein parties, like the brand’s store opening in 1992, where the brunette beauty was hit on by a then-unknown actor.

“He came up and started talking to me. And he was so — it’s a weird word for a man — but so pretty. Beautiful blue eyes, gorgeous face. But almost like, too much,” she said.

“And then he asked me for my number, and I said, ‘Oh, I don’t give out my number.’ And then he just looked at me funny, but kind of smiled a little coyly … He walked away and came back and gave me a little piece of paper with a phone number, and it said ‘Jared Leto.'”