Young Anna Wintour’s 1980s and 1990s Style: Photos

Anna Wintour circa 1990 in New York. Photo:
Sonia Moskowitz/Image/Getty

Fashion is always evolving, and Vogue editor-in-chief Anna Wintour’s personal style has, naturally, evolved right along with it.

Known today for her chunky crystal necklaces, column dresses, and a seemingly endless array of floral prints — not to mention her signature Chanel sunglasses and bob — Wintour has described her current personal style as “safe verging on extremely boring.”

But while the most powerful woman in fashion and the long-time chairperson of the annual Met Gala may feel she’s settled into a chic signature look in her 70s, she was unquestionably a risk-taker during her early years at Vogue.

As next week’s 2024 Met Gala celebrates 400 years of fashion history with its “Garden of Time” theme, we’re time traveling back to the late-'80s and mid-'90s to see how Wintour’s retro ensembles compare to her current wardrobe of garden party frocks.

01 of 15

Go for the Gold

Vogue Editor Anna Wintour attends Metropolitan Museum of Art Costume Institute Gala "The Age of Napoleon - Costume From Revolution To Empire" on December 4, 1989 at the Metropolitan Museum of Art in New York City. — Anna Wintour at the 1989 Metropolitan Museum of Art Costume Institute Gala.
Getty

Sequins, metallics, and glinting get-ups were much more a part of Anna Wintour’s wardrobe in the late '80s than they are now. She absolutely glistened in this gold double-breasted jacket at the Metropolitan Museum of Art’s 1989 Costume Institute Gala. The signature bob was darker and more severe, and the business-like look was a far cry from the slim, floor-length evening gowns she now sports as the event’s chair.

02 of 15

Cold Shoulders

Along with the sparkles, Anna Wintour showed more skin in the late '80s than she does now. The strapless gown she wore to the 1989 Council of Fashion Designers of America (CFDA) Awards is a prime example.

03 of 15

Prints Charming

Anna Wintour during Tiffany's New Men's Fragrance Launch - September 19, 1989 at Tiffany's in New York City, New York, United States. — Anna Wintour in 1989.
Ron Galella/Ron Galella Collection via Getty

Bold prints remain a staple of Anna Wintour’s personal style, but these days she tends to favor colorful florals. The cropped black-and-white animal print jacket she wore to the September 1989 launch of a new men’s fragrance by Tiffany’s is a marked contrast.

04 of 15

Glitterama

British-American editor and journalist Anna Wintour attends a New York Ballet gala at the New York State Theater at Lincoln Center, New York, New York, May 1, 1990. — Anna Wintour at Lincoln Center in 1990.
Ron Galella/Ron Galella Collection via Getty

Anna Wintour cemented her position as the fashion industry's North Star when she took the helm at American Vogue in 1989. A few months into her tenure, her clothes reflected the dose of glamour she injected into the magazine.

05 of 15

Loud and Proud

Has there ever been a more early '90s blouse than this? It practically comes with its own MC Hammer soundtrack!

06 of 15

Fortune Favors the Bold

Vogue Editor Anna Wintour attends Paris Haute Couture Fashion Show and Cocktail Party on September 5, 1990 at the Plaza Hotel in New York City. — Anna Wintour in 1990.
Ron Galella/Ron Galella Collection via Getty

This eye-popping suit Anna Wintour was photographed in circa 1990 is a definite precursor to her flower-powered 2020s style, albeit in a more abstract, retro register.

07 of 15

Going Places

Anna Wintour during Armani Dinner and Screening of "Made In Milan" at Museum of Modern Art in New York City, New York, United States. — Anna Wintour circa 1990.
Ron Galella/Ron Galella Collection via Getty

Anna Wintour’s rise to the top of the fashion and media worlds was seemingly unstoppable. This bright yellow jacket screams “Outta my way!”

08 of 15

Rainbow Connection

Voge Editor Anna Wintour attends the screening party for 'Awakenings' on December 17, 1990 at the Pierre Hotel in New York City. — Anna Wintour in 1990.
Ron Galella/Ron Galella Collection via Getty

Some looks are truly timeless. It’s not hard to imagine an It Girl in 2024 turning heads in this glittering rainbow minidress, as Anna Wintour certainly did in 1990.

09 of 15

Lace Up

Vogue Editor Anna Wintour attends 10th Annual Council of Fashion Designers of America Awards on February 25, 1991 at the Metropolitan Museum of Art in New York City. — Anna Wintour in 1991.
Ron Galella/Ron Galella Collection via Getty

Another example of how Anna Wintour’s penchant for florals has evolved, here they’re cast in exquisitely moody black lace.

10 of 15

Rock Star

While short skirts and lame tops no longer feature prominently in Anna Wintour’s wardrobe, the amber stones in this statement necklace she wore in 1991 echo the multiple strands of crystals she consistently layers today.

11 of 15

Fly Girl

Vogue Editor Anna Wintour attends 12th Annual Burden Awards Honoring Yasmin Aga Khan on December 2, 1991 at Rainbow Room in New York City. — Anna Wintour in 1991.
Getty

Never much of a party animal, today Anna Wintour’s style is elegantly lady-like. But at the 12th Annual Burden Awards at New York City’s Rainbow Room in 1991, she looked like she was ready for a dance-off with the In Living Color crew.

12 of 15

Black Out

Anna Wintour during Party to Unveil Barneys Holiday Window - November 23, 1992 at Barneys New York in New York City, New York, United States. — Anna Wintour in 1992.
Ron Galella, Ltd./Ron Galella Collection via Getty

Anna Wintour is notorious for her alleged distaste for all-black outfits, though that preference may have been overstated. “I am perfectly fine with people wearing black,” she said in a 73 Questions video with Vogue in 2023. Clearly, she was perfectly fine with wearing all-black herself in 1992.

13 of 15

Think Pink

Forget all-black, Anna Wintour is rarely seen a monochrome ensemble of any hue these days. But in the mid '90s, she was more than happy to step out in head-to-toe pink.

14 of 15

Fur-iously Defiant

Anna Wintour arrives with sunglasses attending Metropolitan Museum of Art Costume Institute gala to introduce Gianni Versace Exhibition. — Anna Wintour at the 1997 Met Gala.
Richard Corkery/NY Daily News Archive via Getty

Anna Wintour’s unabashed love of fur made her a figure of controversy for years. But despite drawing notorious protests from animal rights groups like PETA, she’s never shied away from wearing a sumptuous pelt.

15 of 15

Animal Magnetism

Anna Wintour during PEN American Center Gala Honors Arthur Miller at Lincoln Center in New York City, New York, United States. — Anna Wintour circa 1997.
Ron Galella, Ltd./Ron Galella Collection via Getty

Anna Wintour certainly doesn't shy away from leopard print these days, but she's long since eschewed strappy gowns like this one she wore to the PEN American Center Gala at Lincoln Center in 1997.

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