Anna Wintour, the Editor-in-Chief of Vogue magazine, is rarely seen without her iconic sunglasses—the look has become a staple of her public persona. Even in hulu’s 2024 documentary series In Vogue: The 90s, which premiered on September 13, she insisted she’d keep them on during her interview. But there was a time, as a young editor, that Wintour hadn’t discovered the power of shades.
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“No, I’m gonna wear them,” she replied when filmmakers asked if she’d remove them for the documentary. Wintour told CNN in April 2019 that her sunglasses help her “avoid people knowing what [she’s] thinking about.” This allows her to maintain a level of privacy regarding her reactions and feelings, especially in public settings like fashion shows or meetings.
In a more relatable strategy, Wintour also hides behind her sunnies because “they help me when I’m feeling a bit tired or sleepy. And maybe they’ve just become a crutch in part of who I am. But today I really did need them.” She added specifically concerning the CNN interview, “I have been unbelievably ill all week. And, plus, I just had eye surgery, so those are the real reasons I’m wearing them today.” But what does she look like without them?
Take a long these photos of a young Anna Wintour
CFDA Awards
Image Credit: Photo by Fairchild Archive/Penske Media via Getty Images Circa 1990s.
With Kark Lagerfeld
Image Credit: Photo by Sonia Moskowitz/IMAGES/Getty Images With fashion designer Karl Lagerfeld at the 12th CFDA Awards in 1993.
With Sandra Bullock
Image Credit: Photo by Dimitrios Kambouris/WireImage During Fashion Week.
Serving in this tartan suit
Image Credit: Photo by Ron Galella/Ron Galella Collection via Getty Images Circa 1990.
8th CFDA Awards
Image Credit: Photo by Ron Galella/Ron Galella Collection via Getty Images Circa 1989.
Circa 1990
Image Credit: Photo by Sonia Moskowitz/Image/Getty Images Still with the trademark bob.
With her husband David Schaffer
Image Credit: Photo by Ron Galella/Ron Galella Collection via Getty Images At the 1991 CFDA Awards.
With Oprah
Image Credit: Photo by Richard Corkery/NY Daily News Archive via Getty Images In 1998.
Paris Haute Couture Fashion Show
Image Credit: Photo by Ron Galella/Ron Galella Collection via Getty Images Circa 1990.
Pierre Hotel in New York City
Image Credit: Photo by Ron Galella/Ron Galella Collection via Getty Images At the Awakenings New York City screening and party in 1990.
Party for the new Andre Courreges boutique
Image Credit: Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images Circa February 19, 1991.
Made in Milan event
Image Credit: Photo by Ron Galella/Ron Galella Collection via Getty Images On October 31, 1990.
Tiffany’s new men’s fragrance launch
Image Credit: Photo by Ron Galella/Ron Galella Collection via Getty Images On September 19, 1989.
With Calvin Klein
Image Credit: Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images In 1994.
With Princess Diana
Image Credit: Photo credit should read POOL/AFP via Getty Images As well as Washington Post owner Katheryn Graham, designer Ralph Lauren, and Georgetown University President Leo J. O’Donovan.
At the Mario Testino Exhibition
Image Credit: Photo by Dave Benett/Getty Images In 2002.
Met Gala with her husband David Schaffer
In 1994.
In the front row of Celine Paris Fashion Week
Image Credit: Getty Images Winter runway, 2003/2004.
At the American Society of Performers Gala
Image Credit: Photo by Ron Galella, Ltd./Ron Galella Collection via Getty Images May 11, 1995.
Marc Jacobs Spring Summer Collection
Image Credit: Photo by Evan Agostini/Getty Images In 2004.
