Anna Wintour Then vs. Now: See What She Looked Like Through the Years

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, 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