Style Through the Years: Take a fashionable journey through Anna Wintour fashion style evolution, from her early days at Vogue to today.
Some names in fashion are as recognizable as Anna Wintour. The longtime editor-in-chief at Vogue, Wintour has held the title of high priestess of haute couture for upwards of three decades. Wintour’s bobbed haircut, massive shades, and intimidating attitude have not only defined the fashion world but also turned her into an icon of power, elegance, and a classic look.
The 1970s: Getting Started
Before Wintour was synonymous with Vogue, she was an emerging fashion journalist. Wintour was born in 1949 in London and entered the world of fashion at the beginning of the 1970s, serving as the junior fashion editor at Harper’s & Queen in London.
Style Snapshot:
long, straight hair with bangs
blazers and wide-legged trousers
platforms and patterns layered like a reflection of the decade
British flair that was relevant and reflected an experimental yet polished sense of fashion
Wintour’s look at this time might be regarded as bohemian, reflective of the cultural revolution occurring in her words. Although she was not yet the picture of steel, she had captured the essence and element of her tailored elegance.
The 1980s: The Emergence of the Power Woman
During the 1980s, Anna Wintour moved to New York City and quickly made her way up the editing ranks at New York Magazine, then took over British Vogue in 1986 and finally, Vogue US in 1988.
Style snapshot:
Sharp shoulders: power suits
Midi-length skirts with sophisticated blouses
Bold patterns, flowers, and/or eye-catching accessories
The introduction of her bob hairstyle and sunglasses
This decade marked the initiation of her editing uniform: impeccably tailored coats, big necklaces, and a stoic gaze. The bob cut had finally become a permanent fixture on her! Wintour’s look was now authoritative, sleek, and consistently high fashion.
The 1990s: The Queen of Cool
anna wintour fashion style
By the time the 90s arrived, Wintour had established herself as a commanding international authority in fashion. The decade’s wardrobe choices reflected minimalism, supermodels, and grunge, all of which Vogue epitomized.
Style snapshot:
Sleek midi-length Chanel jackets
Slim skirts and high boots
Tailored, sharper coats with classic fabrics
Neutral colors, with the occasional print
While she was certainly nuancing into the 90s’ minimalist choices, Wintour had no problem maintaining sophistication. Her sunglasses were clearly her fashion armor, as she often wore them indoors and at night; they were, and sold, as her favorite accessory.
The 2000s: Regal Glamour and Red Carpets
With red carpet fashion steadily becoming entrenched in pop culture during the 2000s, Anna Wintour’s own fashion sense was already embodying a new level of glamour and high-society persona. Wintour constantly flaunted her style at various fashion weeks, galas, and events.
Style Snapshot:
Luxe evening gowns from Oscar de la Renta, Prada, and Chanel
Floor-length fur coats and embellished capes
Pearls, statement necklaces, and brocade fabrics
Pointy-toe heels and ladylike clutches
You could say that Wintour embraced the title of fashion matriarch with unapologetic pretension; whenever the Met Gala came around, it was typically understood that she would be in pastel-colored, floor-length dresses and bold costume jewelry, though Wintour never prizes excess or ostentation — instead, she always opts for intentful embellishments and accessories.
The 2010s: Masterclass in Consistency
The 2010s were about refinement and consolidation. Anna Wintour did not suddenly reinvent herself – she simply refined herself. For example, Wintour leaned into modern silhouettes but still kept her signature staples.
Style Snapshot:
Feminine floral mid dresses styled with structured jackets
Sheath dresses with bold prints and cropped coats
A rotation of established brands: Chanel, Miu Miu, Carolina Herrera, etc.
Color palettes were neutral, but there was almost always a dotted floral or abstract print (disguised)
Wintour also became influential beyond print media. Her recent work and participation in The September Issue documentary, and in her advisory positions in the CFDA and Vogue Fashion Fund, expanded her aura beyond a renowned tastemaker, but into a global cultural figure.
The 2020’s: Timeless Chic Meets New Wave
At 73 years old Anna Wintour continues to command marvelous interest in her unique and timeless personality. Even though fashion changes constantly, she owns the proverbial red carpet. TikTok fashion stars, Gen Z trends, or any other version of a modern, fashionable icon are not competition for her, instead they only support and expand her potential legend.
Style Snapshot:
Maxi-length floral dresses, layered necklaces
A renewed love for prints, bold patterns, rich fabrics
Updated shapes that are still age-appropriate but stylish
Gently introduced color, contemporary designers, and more casual staples to her wardrobe
Supported up-and-coming designers and still remain loyal to legacy fashion houses. Anna has also completely paved meaningful space for sustainability and diversity, and these important areas have become the foundations of her editorial and fashion week purpose.
Anna Wintour’s Key Style Pickings
Here are the components that have long defined her look:
The Bob – Sleek, shoulder grazing, layered with or without bangs, Wintour’s hair hasn’t changed in relation to any fashion trends, and remains her most recognizable feature.
Sunglasses- incorporate fashion sunglasses as not only a stylish accessory but keep in mind the brand-spaces such as Chanel or Tom Ford to also maintain one’s privacy and mystique.
Floral Dresses – You’ll see Anna in floral and paisley prints, whether at Fashion Week or the Met Gala.
Statement Necklaces – Whether she’s rocking turquoise beads or a diamond choker, one of Anna’s favorite things to wear is interesting neck items.
Manolos or Kitten Heels – Practicality and style sum up her shoe fashion; she wears sophisticated, comfortable shoes.
Fur Coats and Capes – Despite the reduction of real fur since the ethical concerns over fur clothing, she can still serve up the drama and is never without basic outerwear.
A Living Fashion Legacy
Anna Wintour’s fashion journey is not a transformation, it is a timeline of her life through fashion history. From 70s boho editor to couture princess, her life story is the life story of fashion.
What is timeless is not just the bob, the sunglasses, or the florals; it is her commitment to authenticity, her eye for what is next, and the talent she picks to carry her legacy.
As fashion evolves in 2025 and beyond, Anna will always be in style.
FAQs
What designers are most frequently worn by Anna Wintour?
A: Anna Wintour wears a number of fashion houses, often like Chanel, Prada, Oscar de la Renta, Carolina Herrera, and Tom Ford.
Why does Anna Wintour wear sunglasses all the time?
A: She says it is to stop people from reading her facial expressions, especially at fashion shows. The sunglasses help inject an element of mystery.
Has Anna Wintour’s style changed over the years?
A: Anna’s style is fundamentally consistent; however, she has somewhat adapted to some of the newer designers, textures, and more inclusive values.
Is Anna Wintour still the editor of Vogue in 2025?
A: Anna Wintour is still the editor of Vogue as Global Editorial Director and is still a large driving force in the fashion world.
What does Anna Wintour’s style look like?
A: Anna Wintour’s signature look is a bob haircut, oversized sunglasses, printed midi dresses, statement necklaces, and a pair of Manolo Blahniks.
