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1963
Anna's first and only bob, age 14.
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1964
A Biba girl! Anna started her first job at 15, working retail at Biba Boutique.
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1970
Anna at the beginning of her career working as an Editorial Assistant at Harper's & Queen with Jim Lee and Helmut Newton.
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1972
She held down this role for 4 years before moving to America and becoming Junior Fashion Editor of Harper's Bazaar.
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1975
Anna lasted 9 months in her role as Junior Fashion Editor before she was fired for being too 'European' aka provocative.
Fun fact: This was about the time she was obsessed with Bob "Robert" Marley and used to disappear for weekends with him.
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1988
After brief stints at Viva - International Woman's magazine and Home and Garden, Anna became editor in chief of American Vogue.
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1989
Iconic LBD moment.
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1990
Cute in rainbow sequins and shiny dance tights which remain a staple in her wardrobe from here on out. Is she on to something?
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1991
What a lewk! Gold lamé skivvy, tennis skirt and statement jewels. Well before her time, this is very early-2000s. Especially that necklace from Lovisa.
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1991
Anna wearing an oversize puffer to the ballet.
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1993
Fun Anna in a quintessential 90s sweatshirt.
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1994
Super shiny bob to match the satin tangerine shirt.
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1995
Slinking through the mid-90s.
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1995
On vacation with bestie, Donatella Versace.
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1999
We love party girl Anna, and this one-shoulder slip.
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2003
The early 2000s were undoubtedly an era of heavy blonde streaks from which NOBODY was spared, not even madam Vogue. Woah, she 100% influenced the 'can I speak to the manager' haircut.
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2005
A casual Anna in her boot cuts.
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2006
Tête-à-tête with frenemy Andre Leon Talley.
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2008
“If you can’t be better than your competition, just dress better.”
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2011
Anna and her +1 Nicki Minaj at Carolina Herrera.
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2014
Bob on the go.
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2015
Front row at Yeezy with friends Kimmy and North.
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2017
"Nuclear Wintour" - her reputation precedes her.
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2019
At the US Open with Venus and Megan. Tennis is Anna's favourite sport.
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2020
A year of rest and relaxation. The most casual photo of Anna Wintour in the whole internet.