Anna's first and only bob, age 14.
A Biba girl! Anna started her first job at 15, working retail at Biba Boutique.
Anna at the beginning of her career working as an Editorial Assistant at Harper's & Queen with Jim Lee and Helmut Newton.
She held down this role for 4 years before moving to America and becoming Junior Fashion Editor of Harper's Bazaar.
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.
After brief stints at Viva - International Woman's magazine and Home and Garden, Anna became editor in chief of American Vogue.
Iconic LBD moment.
Cute in rainbow sequins and shiny dance tights which remain a staple in her wardrobe from here on out. Is she on to something?
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.
Anna wearing an oversize puffer to the ballet.
Fun Anna in a quintessential 90s sweatshirt.
Super shiny bob to match the satin tangerine shirt.
Slinking through the mid-90s.
On vacation with bestie, Donatella Versace.
We love party girl Anna, and this one-shoulder slip.
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.
A casual Anna in her boot cuts.
Tête-à-tête with frenemy Andre Leon Talley.
“If you can’t be better than your competition, just dress better.”
Anna and her +1 Nicki Minaj at Carolina Herrera.
Bob on the go.
Front row at Yeezy with friends Kimmy and North.
"Nuclear Wintour" - her reputation precedes her.
At the US Open with Venus and Megan. Tennis is Anna's favourite sport.
A year of rest and relaxation. The most casual photo of Anna Wintour in the whole internet.
© 2023 colleen