Anna Wintour's Hair Evolution Proves She Knows Exactly What She Likes

Anna Wintour is arguably one of the most influential fashion enthusiasts in the world. Wintour started her journalism career as a fashion editor for Harper's Bazaar and went on to serve as editor for British Vogue between 1985 and 1987. In 1988, she was named editor-in-chief at American Vogue. Her career is as recognizable as her signature look: a neat pageboy bob, often paired with statement sunglasses.

Throughout her career at Vogue, which spanned four decades, Wintour made a profound impact on the fashion industry. She became the chair of the Costume Institute Gala at the Metropolitan Museum of Art, transforming the Met Gala into a global cultural phenomenon over time. She also pioneered the blending of the fashion world with the political and technological spheres. Wintour revamped the magazine editorial world by featuring leading women on Vogue's covers rather than including only models. Her trailblazing efforts have been recognized in numerous ways, including her appointment as Dame Commander by the British monarchy and her rumored role as the inspiration behind the character Miranda Priestly in "The Devil Wears Prada."

She eventually stepped down from her post as Vogue editor-in-chief in 2025, and as of 2026, Wintour serves as the global chief content officer for Condé Nast. Despite shifting her focus to Vogue's parent company, Wintour remains a leader in the fashion world. Not only is this trailblazer recognized for her spectacular work ethic and for revolutionizing the magazine industry, but her signature look has also garnered plenty of attention.

Wintour has a traditional approach to the fashion world, an attitude she has woven into the Met Gala rules that all attendees must follow, such as no phones and no seat changes. Her old-school nature extends beyond the workplace and to her appearance, as she has maintained the same hairstyle since she was 14. In the 1980s, as pictured above, Wintour donned a brunette pageboy bob with bangs. The ever-fashion-forward icon embraced the statement hairstyle long before micro bobs became popular in the late '80s and early '90s.

By the 1990s, Wintour had grown out her fringe and welcomed a lighter hair color. She showcased her updated hairstyle at New York Fashion Week in 1998. While she maintained her signature bob, she swapped her dark brunette hair color for a soft chestnut brown with ash tones. By maintaining her bold haircut throughout a decade characterized by minimalism, Wintour confirmed her timeless taste — and her hairstylist, Joey Scandizzo, agreed. "Bobs will never go out of style," he told Honey Style in 2019.

Wintour returned to brunette for a brief stint in the early 2000s. The fashion enthusiast dyed her hair chocolate brown for a fall fashion show during New York Fashion Week in 2001. The dark color made her face appear porcelain and enhanced her blue eyes. At this point, Wintour's fringe had grown out even further, completely concealing her eyebrows and grazing her eyelids. Considering brown has long been a staple of fall fashion, Wintour knew exactly what she was doing when she embraced a darker hairdo for that seasonal fashion show.

By the mid-2000s, Wintour stepped out with heavy blonde streaks in her hair. In direct contrast to her natural brunette shade, the fashion icon's platinum blonde highlights at Olympus Fashion Week in 2004 were hard to ignore. Chunky highlights made sense at the time. This hairstyle is essential when it comes to Y2K hairstyle trends. The style was popularized by prominent artists at the time and was seen on celebrities like Kelly Clarkson and Christina Aguilera. While Wintour's hair length remained the same, perfectly resting in line with her chin, her bangs had been trimmed and her eyebrows were more visible.

Later in the 2000s, Wintour finally committed to being a blonde. At the 2006 U.S. Open, despite wearing her signature sunglasses, the fashion icon looked remarkably different with honey-blonde hair. Her warm locks suggested she had long been considering a hair change, and she knew exactly how she wanted to do it. In retrospect, she had clearly been easing herself into a blonde transformation years prior — one of her most drastic hair changes to date. Her gradual transition to blonde also reinforced her structured and controlled public image.

Wintour once again returned to a darker hair color in the mid-2010s. At the Burberry London in Los Angeles event in 2015, the fashion icon was photographed wearing a mousy brown hairstyle. Despite her understated look, her muted brown hair color was elevated by a crystal necklace and the glossy, feathered dress she wore to the event. Wintour's hair transformation was subtle yet chic, and her honey-blonde undertones gave her appearance a natural glow. By gradually embracing darker tones, the fashion mogul foreshadowed her full return to brunette hair in the years that followed.

Mirroring her earlier transition to blonde hair, Wintour had slowly become a full brunette by the late 2010s. During London Fashion Week in 2019, at a Christopher Kane catwalk show, the fashion icon posed with chestnut locks. As her micro-bob framed her face, her darker-toned hair added a sleekness to her look, particularly when paired with her signature sunglasses and a fur-trimmed leather jacket. Despite returning to brunette, Wintour didn't revisit the deep brown shade she wore in the '80s, with her hair still retaining a natural glow.

At Paris Fashion Week in 2022, the fashion mogul revealed a new hair color. This time, she opted for a lighter shade, but her hair had also been trimmed significantly shorter than in previous years and rested slightly above her chin. This hairstyle combined with her dress made for a spectacular look that reminded everyone why Wintour always ranks among the best-dressed women over 40 in every event she attends. While she hadn't hinted towards a return to blonde in the years leading up to her big change, as she had before, Wintour likely sensed her hair needed brightening for the summer of 2022.

As the alleged inspiration behind Miranda Priestly, Wintour was invited to the world premiere of "The Devil Wears Prada 2" in New York in 2026. At this event, the fashion enthusiast showcased her new honey-blonde locks, still on her pageboy bob. While she has dyed her hair numerous times throughout her career, by consistently switching between her mousy-brown color and blonde shades, Wintour has proven she knows exactly what she likes by holding on to her iconic bob.