There are few styles more iconic within the fashion industry than Anna Wintour's hair. According to Business Insider, the Condé Nast chief content officer and Vogue global editorial director has been wearing a bob since she was 15 years old. Although there have been variations over time — like a hint of honey highlights or a deeper brunette hue — the consistency has become as recognizable as the fashion legend herself. (Or, the fully tinted sunglasses she often wears.)
"I've had many hairdressers over the years and I can't remember how long I've had this haircut for," Wintour told Rihanna in a video for the Go Ask Anna series on Vogue's YouTube channel. "The one time I tried to change, it was a disaster. I had to wear a hat for several months. So I'm way too anxious and too lazy to try it again."
Though only Wintour herself would deem anything about the poised bob, neat bangs, and carefully blunt lengths "lazy." Below, take a walk through memory lane and see how Wintour has styled her signature bob over the years. As mentioned before, there are a few tiny details to look out for, like a subtle variation in color — naturally, the famed editor and director has a sharp eye for details.
Anna Wintour's Hair: The 80's
Cropped right at the chin and richly brunette, Anna Wintour's hair in this 1989 snapshot epitomizes the avant-garde cool that prevailed in the late '80s.
Anna Wintour's Hair: Early '90s
Photographed here in 1991, Wintour's bob is slightly more grown out with a hint of richer, redder tones throughout. The bangs appear more uniform than wispy, as well.
Anna Wintour's Hair: Late '90s
The straight, blunt bangs and mysterious sunglasses get paired together in the late '90s. Though it might be the lighting of this 1999 photo, it looks as if Wintour has embraced a few lighter, blonder highlights.
Anna Wintour's Hair: Early 2000s
Deep brunette Wintour returns in 2002, though the straight-across bangs stick around.
Anna Wintour's Hair: Mid 2000s
But wait! The blonde highlights came right back as well, edging on platinum in this 2003 picture.
Anna Wintour's Hair: Late 2000s
Wintour continued to play with blonder shades for the rest of the 2000s, settling on this dark honey hue in 2009 that's oh-so recognizable now.
Anna Wintour's Hair: Early 2010s
Wintour's warm-toned bronde is still here, though it's interesting to see how the fashion leader embraced slightly looser hair in the 2010s. Here, her bob has less of a flip or curl at the end, creating a sharp silhouette with the sunglasses.
Anna Wintour's Hair: Late 2010s
Wintour traded out the noticeable highlights for a more contemporary, one-tone shade — very 2018.
Anna Wintour's Hair: 2020
Somewhere between a redhead, brunette, and blonde, Wintour's deep strawberry blonde continued to 2020, as did the straight bangs. Though after a few decades with the stylish cut, those probably aren't going anywhere any time soon.