Every time Anna Wintour proved why she's the Queen of Fashion - from unexpected looks to chic couture

There are certain people who have that special something that makes them a true force to be reckoned with. Take Anna Wintour, for example; even those who aren't interested in fashion know who she is.

For decades, she has been setting trends, making designers household names and breaking down barriers for fashion and culture.

While certain things - like her blunt bob and dark sunglasses - remain constant, Anna Wintour has undergone a significant style evolution over the years. She's never been afraid to shy away from risks either, which is why she's an undisputable fashion great.

32 times Anna Wintour proved why she's the queen of fashion

Her first Met Gala in charge, 1995

In 1995, Anna Wintour officially took over the responsibly of co-chairing the annual fundraiser aimed at helping the Costume Institute of the Metropolitan Museum of Art. This would, of course, go on to become the biggest fashion event of the year and is best known as the Met Gala.

For her debut as a co-chair, Anna went for old-school, unabashed glamour in a floor-length, silky, halter-neck gown with matching opera gloves.

The theme that year - Haute Couture – certainly called for some all-out elegance and finery, and Anna led by example.

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Based on extensive interviews with Anna Wintour's friends and collaborators, including some of the biggest names in fashion, journalist Amy Odell charts the rise of the fashion powerhouse, from her tomboyish childhood days to her status as the most powerful woman in media.

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Met Gala, 2015

The legendary Vogue editor-in-chief famously eschews an all-black ensemble, favouring colours and prints.

For the 2015 Met Gala, which had a theme of China: Through the Looking Glass, she walked the walk when it comes to this adoration of loud and proud styling, wearing an extravagant, eye-catching Chanel couture creation complete with sequinned flower embroidery.

The bloom of red flower details included larger poppies around the collar and waist, while the added touch was the flourishing shoulder detailing.

Met Gala, 2003

The theme of 2003’s Met Gala was Goddess, and Anna Wintour’s co-chairs included fashion legend Tom Ford and acting royalty Nicole Kidman.

Anna Wintour went against one of her well-known fashion rules and opted for a monochrome style. Wearing a heavenly white silk dress with a matching fringed shawl-style cardigan which almost resembled angel wings.

To break up the serene white, Anna wore her trademark dark sunglasses.

Chasing rainbows, 1990s

The editor-in-chief was always a name in high society circles, even before she’d earned her decades of prestige leading Vogue.

Proving that she had a timeless knowledge of fashion, Anna was spotted around New York City rocking a daring, sequin mini dress in a rainbow colourway.

A scene-stealing number even back then, this mini wouldn’t look amiss on today’s red carpets.

Anna's LBD

Everyone needs their very own LBD – a little black dress. It’s the simplest way to always have something glamorous tucked away for any occasion, and in 1989, Anna Wintour rocked her corseted Chanel dress which she paired with glittering long sleeves.

She accessorised with a statement chunky necklace.

Shining bright in metallic

Attending the grand opening of Galeries Lafayette in March 1991, Anna Wintour proved that she could master the sometimes-difficult trend of metallic.

The chic editor let her outerwear do the heavy lifting, keeping her gold, metallic trench coat the focal point of her outfit. With a cinched in waist and more width at the hem, the heavy outerwear mirrored a classic, elegant silhouette.

Met Gala, 2021

For the 2021 Met Gala – which followed the theme, In America: A Lexicon of Fashion – Anna Wintour arrived on the scene like a breath of fresh spring air. Almost literally.

Dressed in a burst of floral colours, the iconic editor wore a floor-length Oscar de la Renta floral gown which featured a mermaid silhouette and a ruffled train.

CFDA Awards, 2023

For the uber-glamorous CFDA Awards (The Council of Fashion Designers of America) in 2023, Anna Wintour mingled with the likes of Serena Williams and Naomi Campbell.

For the occasion, Anna played with a greyscale colour palette, which included a floor-length printed dress and an icy-white, fluffy coat. She also wore ankle boots with a grey and white stripe design.

The De Vil wears Dalmation

Anna Wintour has a reputation for being tough – the Devil Wears Prada was written by a former staffer and is thought to be inspired by her time working for the editor-in-chief, albeit exaggerated.

Doing nothing to soften that image, this amusing outfit complete with a Dalmatian print jacket screams Cruella De Vil, one of the all-time villains we can't but help love to hate.

Elevated every day basics

As one of the biggest names in fashion, Anna Wintour has access to all the designers. But not every outfit needs to come with bells and whistles to be chic and practical.

Case in point, attending New York Fashion Week in 1996 rocking some capsule wardrobe essentials – a well-fitted, white knit jumper and tailored grey trousers were good enough to keep her going from front row to front row.

Going for gold

Anna Wintour attended the 1989 Met Gala which had a theme of The Age of Napoleon: Costume from Revolution to Empire.

Never one to defy a theme, Anna’s chosen outfit – a gold, double-breasted jacket – felt almost military-inspired, or like a coat of armour.

With her signature sleek bob and six strings of pearls giving added texture around the neckline, the legendary editor won the battle for best dressed.

CFDA Awards, 2022

For the 2022 CFDA awards, Anna Wintour relied on one of her firm fashion favourites – Chanel. The fashion icon sported a red, tweed ensemble which came right off the runway.

Anna’s whole co-ordinated ensemble was taken from the Fall-Winter 2022/23 Haute Couture collection from the French fashion house.

Bold prints, 1990

Anna Wintour has never shied away from the fact she prefers colours and prints to all-black outfits. In more recent years, Anna has worn head-to-toe prints and patterns for the likes of the Met Gala, and, as this loud and proud ensemble proves, she’s been doing this for decades.

Anna attended a Paris Haute Couture Fashion Show and Cocktail Party at Paramount Hotel in New York City in 1990 wearing a graffiti-style dress with matching cardigan. In addition to the abstract patterns and pops of colour, both items included contrast white trim.

Met Gala, 2006

London-born Anna co-chaired the 2006 Met Gala which had a nod to her own roots; the theme was AngloMania: Tradition and Transgression in British Fashion.

While Anna didn’t choose an English designer – she stuck with Chanel – her look screamed regal Britishness. From the majestic, blush pink cape to the roses on the sequin gown, it was on theme and a memorable style moment.

Showcasing her wild side

In 1997, the reserved editor-in-chief proved she wasn’t averse to a walk on the wild side – unleashing a full-length animal print dress. Anna’s strappy, cheetah print gown was slinkier than what she's worn in recent years, and she let the sexy gown take centre stage by keeping her accessories to a bare minimum.

Statement outerwear

If there’s one lesson to take from Anna Wintour’s decades in fashion, it’s the power of a statement piece. While attending a Victoria Beckham fashion show, Anna wore a sweeping, red leather trench coat. For this occasion, she kept everything tonal, with a lighter shade of red adding depth to the style without distracting from the coat.

Reimagining the military coat

Attending the Erdem 2024 Ready-to-Wear show, Anna Wintour arrived sporting several of her trademark style staples.

From the dark sunglasses, the statement outerwear and pops of floral, it was elevated Anna. The heavy, forest green khaki coat had embroidered floral detailing, and Anna subtly let her deep red dress underneath peek out and contrast with the coat.

US Open, 2022

If you ever wanted to see Anna Wintour drop that trademark impenetrable facial expression, take her to a tennis match. A known lover of the sport, Anna attended the 2022 US Open to watch Serena Williams in the Grand Slam. She wore a flowing, floral blue dress for the occasion and surprisingly laid-back shoes – a pair of striped espadrilles.

Vintage Chanel

Anna Wintour’s love of Chanel is well-known – she’s worn Chanel to nearly every one of her Met Gala appearances and she was married in a Chanel wedding dress in the 1980s. When she was cementing her status as a force in publishing, her go-to power uniform was a classic Chanel boucle jacket and matching skirt. Vintage glamour, in a daring, courageous red.

Sequins

She might have cultivated a tough, intimidating image, but Anna Wintour has always done incredible acts of charity. In the 1990s, at the height of the AIDS epidemic, Anna galvanised the fashion community by running an event where everyone could shop for designer items and special items with all proceeds going towards AIDS research.

The event – known as 7^th on Sale - raised millions. Proving you can do good and look good, Anna lit up the event in a sequin ensemble.

GQ Global Creativity Awards, 2023

Anna Wintour attended GQ’s first ever Global Creativity Awards in 2023, and she chose a creative ensemble that really showcased her love of colour and patterns.

Anna’s silky, floor length dress included a rich green body and ivory hem, with floral motifs printed across. The block colourways appeared to give Anna more height, and the straight draping and long sleeves made her look svelte and statuesque.

Anna Wintour in… jeans?

In 2001, hell did not freeze over, but Anna Wintour really did step out on the red carpet wearing a t-shirt and jeans. She was hosting the VH1/Vogue Fashion Awards, and her very Americana outfit was a nod to New York City which was recovering after the terror attacks on 9/11.

New Yorkers for Children Gala

Forget the ice queen reputation, Anna was all fire and heat for a special gala in New York City. Anna Wintour oozed pure, romantic glamour as she relied on her trademark love of bold colours. Wearing scarlet red which she complemented with a subtle touch of blush – a rare deviation from her usual glam – Anna’s red dress was a one-shoulder, silky creation.

Met Gala, 2018

The theme of the 2018 Met Gala was Heavenly Bodies: Fashion and the Catholic Imagination, and Anna Wintour still found a way to make Chanel work for the occasion.

The icon stepped out playing a character, no less, telling reporters she was wearing Cardinal Chanel, a nod to her loyalty to the brand.

As Cardinal Chanel, Anna wore an elaborate white-gold dress with a high neck and a diamond rosary necklace.

Anna wears Prada

In 2018, the editor wore Prada as she was honoured with the Visionary Award at the LGBTQ Center in New York.

Wearing a floral Prada dress with a matching overcoat, Anna commented, "I believe with all my heart that we’re headed toward a brighter moment than the one we’re living through right now, a future where everyone is accepted for exactly who they are."

Red tartan

She may have made New York City her domain, casting a detailed eye (behind sunglasses) over the fashion capital for decades, but Anna Wintour never forgets her British roots. In early 1990, she attended a book launch wearing a bright and bold red tartan ensemble.

The pattern felt distinctly Scottish, and the material appears to be tweed-like. However, there’s a sense of American drama in the oversized shoulders – a nod to the end of the 1980s excess where budgets, silhouettes and hair were bigger.

Burberry, 2013

The fashion queen attended the Burberry Prorsum show at Kensington Gardens in 2013 wearing a soft cyan boat neck coat. With the open-neck style, Anna allowed a peek at her outfit underneath, which appeared to be a darker blue dress, once again playing with the idea of tonal dressing.

Met Gala, 2008

For 2008’s Met Gala - Superheroes: Fashion and Fantasy – Anna appeared on the red carpet completely embodying the theme, looking like an epic sci-fi creation in a silver Chanel gown designed by Karl Lagerfeld. The dress featured shell-shaped padding along the waist and shoulders.

The Annual Night of Stars, 2002

Anna Wintour’s fashion choices weren’t always so certain – today, it’s more likely than not that she’ll wear something floral or flowing. But in the early 2000s, Anna stepped out for the Night of Stars gala in a flattering, ruched velvet dress in a deep, merlot red.

The mermaid tale and ruching effect gave a flattering shape, while the warm colour looked radiant against her fair skin. When outside and braving the cold, Anna paired her velvet dress with a grey fur stole.

Met Gala, 1997

The 1997 Met Gala was tinged with sadness, honouring the late Gianni Versace who had been shot dead that same year. Perhaps as a nod to her friend, who famously favoured all things lavish and excessive, Anna upped the ante and went with larger-than-life glamour.

The fashion icon stepped out with a statement jacket - one of her style staples - which included a large, reddish fur lapel. Underneath, she opted for a very Versace slinky, silver slip dress.

Thinking pink

Barbiecore was one of the dominant trends in 2023 following the release of the Margot Robbie fronted movie, but trust Anna Wintour to have completely mastered the look decades earlier.

In 1996, for the opening of a new Chanel store in New York, Anna stepped out in head-to-toe pink. She wore different shades of the colourful hue for an added touch of chicness, and the silky, satin material added an elevated feel.

Met Gala, 2019

Camp: Notes on Fashion was the theme for the 2019 Met Gala, and many fashion experts were eager to see how the celebrities would tackle such a playful idea.

Well, never one to deviate from a theme, Anna Wintour led by example by adding fun touches to her trademark style notes. While she stuck with Chanel (of course), she added cute, campy touches with sequinned, pastel flowers on the floor-length gown.

For a final flourish, she wore a pink and purple feathery stole that glided down to her thighs. It was part princess, part performance, and perfectly camp.