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Princess Diana's Most Memorable Style Moments

50 Reasons Princess Diana Will Forever Be Our Style Icon

Nov 5 2020

Behind every great style icon is another great style icon. We wouldn't have our Victoria Beckhams without Audrey Hepburn. Where would the Kardashians and Jenners be without Marilyn Monroe? And we would argue that Catherine, the Duchess of Cambridge might have a touch less glamour if she weren't following in the formidable footsteps of Princess Diana. Hey, you don't get a Dior bag named after you for nothing!

We're looking back at her most memorable fashion moments — from the diamonds to the wellies — to celebrate the bold, showstopping, and unapologetic choices that made her the people's princess. While they all may be from another decade, much like Diana herself, each look is totally timeless.

Image Source: Getty / Tim Graham

The Wedding Gown

Long before Kate's long-sleeved wedding gown, there were Princess Diana's puff sleeves. Worn before an audience of 750 million eager eyes at the royal wedding on July 29, 1981, the decadent David and Elizabeth Emanuel design set the trend for '80s brides with its ruffles and volume.

Image Source: Getty / David Levenson

Something Blue

When Princess Diana debuted her ring in the royal couple's engagement photo in 1981, no other color would do. Her rich cobalt suit perfectly complemented that famed sapphire stone — not to mention her blue eyes.

Image Source: Getty / Hulton Deutsch

The Revenge Dress

When Diana stepped out for the Serpentine Gallery's annual Summer party in 1994, she was determined to wow. She did just that in an off-the-shoulder Christina Stambolian LBD that was so sexy it became known as "The Revenge Dress."

Image Source: Getty / Anwar Hussein

A Second Revenge

Not to be outdone the following year, Diana returned to London's Hyde Park for the 1995 Serpentine in a beaded cocktail dress from her go-to designer Catherine Walker.

Image Source: Getty / Tim Graham

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A Princess Moment

That was far from the first time she turned to Catherine Walker for a statement look! Princess Diana set out to channel Grace Kelly in the London-based designer's icy chiffon gown at the 1987 Cannes Film Festival. Mission accomplished!

Image Source: Getty / Tim Graham

A Star Is Born

When in Rome — make that America! Princess Diana dressed the part to mingle with Hollywood's elite at the White House in 1995 and turned heads as she twirled with John Travolta in her elegant Victor Edelstein gown.

Image Source: Getty / Anwar Hussein

Sweater Weather

Princess Diana could always be counted on to dress the part — whether that was a red carpet or a trip to the countryside. For a visit to the Craigowan Lodge on the Balmoral Estate in Scotland, she kept to tradition in a cozy Fair Isle sweater and rugged wellies.

Image Source: Getty / Anwar Hussein

Ski Bunny

In 1991, the hands-on mom hit the slopes in Austria in a quintessentially '90s ski suit that proved this was one royal who wasn't afraid to get down (and dress down).

Image Source: Getty / Anwar Hussein

Going With the Flow

For a 1996 trip to Sydney, Australia, Diana was dripping in Chopard diamonds and liquid Versace. The image was so memorable that costume designer Julian Day re-created the look for Naomi Watts's 2013 biopic.

Image Source: Getty / Anwar Hussein

From Princess to King

Princess Diana was the picture of royalty when in Hong Kong for a 1989 visit. To complement her tiara, a wedding gift from the queen, she selected a pearl- and sequin-encrusted Catherine Walker two-piece, which she dubbed her "Elvis Dress."

Image Source: Getty / Tim Graham

New Mom Glow

Princess Diana stood on the steps of St. Mary's Hospital in London in 1982 to greet adoring fans waiting to catch a glimpse of the newborn Prince William. If the playful print looks familiar, it's with good reason.

Image Source: Getty / Anwar Hussein

Bond Girl

Princess Diana looked every inch the movie star when she arrived to the 1985 premiere of James Bond's A View to a Kill in a pleated lamé Bruce Oldfield gown.

Image Source: Getty / Tom Wargacki

Versace

Matchy-matchy doesn't only apply to the royal family's suits! Diana paired her purple Versace gown with Jimmy Choo accessories at a gala dinner at Chicago's Field Museum of Natural History in 1996.

Image Source: Getty / Tim Graham

Versace Versace

Returning to coordinated Versace, but this time in her favored casual silhouette, the suit, Diana arrived at the Buenos Aires Airport for a visit to Argentina in 1995.

Image Source: Getty / Tim Graham

Versace Versace Versace

Another day, another Versace. Princess Diana threw caution to her "Shy Di" persona in a decidedly sexy white slip dress at a 1995 charity concert in Italy.

Image Source: Getty / Tim Graham

Golden Girl

While in Liverpool in 1995, Diana proved she wasn't shy about color either in a marigold Versace suit.

Image Source: Getty / Anwar Hussein

Suit of Armour

You guessed it . . . Versace. This time, Princess Diana complemented her blue eyes in an icy style while arriving to London's Royal Brompton Hospital in 1997.

Image Source: Getty / Tim Graham

English Rose

The royal wore a blue silk Bruce Oldfield gown to a 1982 charity fashion show. Of Princess Diana's presence, the British couturier once called her "a very elegant, confident woman who could look down the lens of any camera."

Image Source: Getty / Anwar Hussein

Pink Lady

Paging Jackie O! The princess channeled another style icon in Versace's pink suit and a pillbox hat in 1995 while arriving to greet the troops.

Image Source: Getty / Tim Graham

Town and Country

While on her honeymoon in Scotland in 1981, Princess Diana dressed the part in a brown tweed suit by Bill Pashley.

Image Source: Getty / Anwar Hussein

On the Dot

Princess Diana was spotted with Queen Elizabeth in Nigeria while visiting in a demure blue suit in 1989.

Image Source: Getty / Princess Diana Archive

The Match Game

When your necklace is as incredible as Diana's emerald stunner, why try to show it up? The princess coordinated her rich green gown to her jewels while in London in 1988.

Image Source: Getty / Georges De Keerle

White Swan

Princess Diana echoed the grace of the English National Ballet dancers while taking in a production of Swan Lake in 1989 in Catherine Walker's column.

Image Source: Getty / Tim Graham

Blue Swan

Princess Diana returned for an encore performance of Swan Lake in 1997 wearing a sheath from her close friend and frequent collaborator Jacques Azagury.

Image Source: Getty / Anwar Hussein

On a Boat

While on her honeymoon cruise in 1981, Princess Diana flaunted her yacht style in a breezy floral design.

Image Source: Getty / Anwar Hussein

Prep School

A more casual look than the diamonds and gowns, Diana looked ever the icon in her gingham capris while unwinding on her porch in Highgrove, Gloucestershire, in 1988.

Image Source: Getty / Tim Graham

Pretty in Pink

Another, but entirely different, pink look from Princess Diana came in 1983 when she wore a Victor Edelstein dress and family tiara in Brisbane, Australia.

Image Source: Getty / Anwar Hussein

Put a Belt on It

While in Majorca, Spain, on vacation in 1987, Diana showed the world how resortwear is done in a relaxed belted shirtdress.

Image Source: Getty / Anwar Hussein

Get Back

No wonder Bruce Oldfield was a go-to designer! This plunging red gown worn in Melbourne, Australia, in 1985 proved the designer made Diana look great from every angle.

Image Source: Getty / Tim Graham

Seeing Red

In 1988, Diana dined with the British Embassy in Paris wearing a red one-shoulder Catherine Walker gown. Not only were the two frequent collaborators, but the designer was also a close friend who was chosen for the princess's burial dress.

Image Source: Getty / Georges De Keerle

Far and Away

While in Abu Dhabi in 1989, Diana dressed the part in a crisp caftan and white trousers.

Image Source: Getty / Anwar Hussein

A Classic

A rose by any other name . . . Diana arrived to a performance of Romeo and Juliet at the Royal Opera House in Covent Garden in 1989 wearing a blue floral gown.

Image Source: Getty / Georges De Keerle

Dressed-Down Beauty

Wearing another casual look, this time a whimsical Smith's Lawn sweater at a polo match in 1983, Princess Diana proved she had elegance no matter what the occasion.

Image Source: Getty / Princess Diana Archive

Anchors Away

Before becoming a princess, Lady Diana wore a nautical ensemble while posing with Prince Charles and Queen Elizabeth at Buckingham Palace in 1980.

Image Source: Getty / Bettmann

In Black and White

At a Plácido Domingo concert in 1992, she bared her shoulders in a two-toned halter dress.

Image Source: Getty / Anwar Hussein

Read Her Shirt

Diana supported the British Lung Foundation while walking the polo grounds with Prince William in 1988.

Image Source: Getty / Tim Graham

Going Down Under

While in Alice Springs, Australia, in 1983, the princess was the picture of casual elegance in a flowy yellow dress.

Image Source: Getty / Tim Graham

Years in the Making

More than 30 years before Prince William and Kate Middleton posed before Ayers Rock in Australia, Prince Charles and Princess Diana took a similar shot. Both men opted for khaki while Middleton paid tribute in a white dress.

Image Source: Getty / Anwar Hussein

Off-Duty Style

While still a fiancée to the prince, Diana kept a low profile in pinstripe trousers in 1980.

Image Source: Getty / Hulton Archive

Soccer Mom

Princess Diana played the part of mom while walking Princes William and Harry to school at Eton College in 1995.

Image Source: Getty / Anwar Hussein

Bold Choice

While in Kuwait City in 1989, Diana paired a daring color combo with a Catherine Walker suit and a Philip Somerville hat.

Image Source: Getty / Anwar Hussein

Dotted Line

Sticking to her print of choice, Princess Diana played with a young Prince William while in New Zealand in 1983.

Image Source: Getty / Anwar Hussein

Princess MacGyver

And sticking to her hue of choice, Princess Diana danced the night away in a one-shoulder gown in Melbourne in 1985. Her standout accessory, borrowed from Queen Elizabeth and commissioned by Queen Mary, was an emerald choker worn as a headband.

Image Source: Getty / Tim Graham

Stand and Deliver

Princess Diana visited the Royal Military Academy Sandhurst in 1987 in a fittingly embellished Catherine Walker design.

Image Source: Getty / Anwar Hussein

Check Mate

In 1990, Diana toured Japan in a plaid coat dress designed by — you guessed it — Catherine Walker.

Image Source: Getty / Tim Graham

Parisian Chic

While in Versailles in 1994, Princess Diana once again turned to Catherine Walker for a standout number. This black halter gown was accessorized with elegant pearl drop earrings.

Image Source: Getty / Anwar Hussein

Ballet Beauty

In 1987, Princess Diana attended a gala performance by The Royal Ballet at The Berlin Opera House in Catherine Walker's grand ballgown. The pink design was later displayed among other memorable archive pieces at Diana: Her Fashion Story, an exhibit currently on view at Kensington Palace.

Image Source: Getty / Tim Graham

Divot Stomping

At a 1983 polo match in Cirencester, England, Princess Diana looked polished in black and white separates with full shoulders and a cinched waist.

Image Source: Getty / Tim Graham

Something Borrowed

Princess Diana turned to an old style trick while dining with the Emperor Hirohito in Japan in 1988 in a Yuki gown. She reset diamonds and sapphires from a watch to wear as a headband.

Image Source: Getty / Anwar Hussein

A True Beauty

But perhaps our favorite look is one that showed both her inner and outer beauty at once. While visiting a landmine minefield in Angola on behalf of The HALO Trust, Princess Diana picked a modest pairing of a white button-down and khaki capris. And she never looked better!

Image Source: Getty / Tim Graham

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