50 of Princess Diana's Most Iconic Style Moments

Princess Diana's iconic style moments have influenced the likes of royals Kate Middleton and Meghan Markle, who have only followed in her footsteps, taking notes from her rulebook as to classic prints, sophisticated silhouettes, and inherited family jewelry reserved for specific occasions. From fashion spectacles such as her Elizabeth and David Emanuel wedding gown — featuring pouf sleeves and a 25-foot long train, and inspiring the replica Kristen Stewart wore in Pablo Larraín's 2021 film "Spencer" — to her iconic Christina Stambolian "revenge dress," Diana's wardrobe will be admired for years to come.

HBO's new documentary "The Princess" spotlights many of the times Diana's outfits were in the spotlight. "She's wearing diamond drop earrings lent by her mother. You want her shoes?" a reporter says excitedly during a live forecast from Diana and Charles's wedding at Buckingham Palace in 1981. "We should all be able to wear wedding dresses and celebrate!" a woman in the crowd gushes, as others are shown obsessing over the intricate details of the bridal look. The documentary footage emphasizes just how much importance was placed on the clothing choices made by the Princess of Wales, which is why all 50 of these appearances will go down in history, sporadically inspiring designer replicas, such as the famous red, white, and black sheep jumper she wore to a polo match in 1983, clad with a prim bow collar.

Ahead, scroll through Princess Diana's most-talked-about gowns, day dresses, sweaters, skirt suits, and trousers.

Additional reporting by Randy Miller

Princess Diana's Style: The Wedding Gown
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Princess Diana's Style: 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.

Princess Diana's Style: Something Blue
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Princess Diana's Style: 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.

Princess Diana's Style: The Revenge Dress
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Princess Diana's Style: 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."

Princess Diana's Style: A Second Revenge
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Princess Diana's Style: 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.

Princess Diana's Style: A Princess Moment
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Princess Diana's Style: 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.

Princess Diana's Style: A Star Is Born
Getty | Anwar Hussein

Princess Diana's Style: A Star Is Born

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.

Princess Diana's Style: Sweater Weather
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Princess Diana's Style: 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.

Princess Diana's Style: Ski Bunny
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Princess Diana's Style: 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).

Princess Diana's Style: Going With the Flow
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Princess Diana's Style: 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.

Princess Diana's Style: From Princess to King
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Princess Diana's Style: 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."

Princess Diana's Style: New Mom Glow
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Princess Diana's Style: 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.

Princess Diana's Style: Bond Girl
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Princess Diana's Style: 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.

Princess Diana's Style: Versace
Getty | Tim Graham

Princess Diana's Style: 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.

Princess Diana's Style: Versace Versace
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Princess Diana's Style: 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.

Princess Diana's Style: Versace Versace Versace
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Princess Diana's Style: Versace Versace Versace

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

Princess Diana's Style: Golden Girl
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Princess Diana's Style: Golden Girl

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

Princess Diana's Style: Suit of Armor
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Princess Diana's Style: Suit of Armor

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.

Princess Diana's Style: English Rose
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Princess Diana's Style: 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."

Princess Diana's Style: Pink Lady
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Princess Diana's Style: Pink Lady

The princess had a Jackie Kennedy moment in Versace's pink suit and a pillbox hat in 1995 while arriving to greet the troops.

Princess Diana's Style: Town and Country
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Princess Diana's Style: Town and Country

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

Princess Diana's Style: The Match Game
Getty | Georges De Keerle

Princess Diana's Style: 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.

Princess Diana's Style: White Swan
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Princess Diana's Style: 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 sheath.

Princess Diana's Style: Blue Swan
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Princess Diana's Style: 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.

Princess Diana's Style: On a Boat
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Princess Diana's Style: On a Boat

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

Princess Diana's Style: Prep School
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Princess Diana's Style: 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.

Princess Diana's Style: Pretty in Pink
Getty | Anwar Hussein

Princess Diana's Style: 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.

Princess Diana's Style: Put a Belt on It
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Princess Diana's Style: 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.

Princess Diana's Style: Get Back
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Princess Diana's Style: 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.

Princess Diana's Style: Seeing Red
Getty | Georges De Keerle

Princess Diana's Style: Seeing Red

In 1988, Diana dined at 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.

Princess Diana's Style: Far and Away
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Princess Diana's Style: Far and Away

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

Princess Diana's Style: A Classic
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Princess Diana's Style: 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.

Princess Diana's Style: Dressed-Down Beauty
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Princess Diana's Style: 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.

Princess Diana's Style: Anchors Away
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Princess Diana's Style: 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.

Princess Diana's Style: Read Her Shirt
Getty | Tim Graham

Princess Diana's Style: Read Her Shirt

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

Princess Diana's Style: Going Down Under
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Princess Diana's Style: Going Down Under

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

Princess Diana's Style: Years in the Making
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Princess Diana's Style: 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 to this very moment in a white dress.

Princess Diana's Style: Off-Duty Style
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Princess Diana's Style: Off-Duty Style

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

Princess Diana's Style: Soccer Mom
Getty | Anwar Hussein

Princess Diana's Style: Soccer Mom

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

Princess Diana's Style: Bold Choice
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Princess Diana's Style: Bold Choice

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

Princess Diana's Style: Dotted Line
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Princess Diana's Style: Dotted Line

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

Princess Diana's Style: Princess MacGyver
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Princess Diana's Style: Princess MacGyver

Sticking to her color 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.

Princess Diana's Style: Stand and Deliver
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Princess Diana's Style: Stand and Deliver

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

Princess Diana's Style: Check Mate
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Princess Diana's Style: Check Mate

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

Princess Diana's Style: Parisian Chic
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Princess Diana's Style: 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.

Princess Diana's Style: Ballet Beauty
Getty | Tim Graham

Princess Diana's Style: 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 that was on view at Kensington Palace.

Princess Diana's Style: Divot Stomping
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Princess Diana's Style: 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.

Princess Diana's Style: Something Borrowed
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Princess Diana's Style: 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.

Princess Diana's Style: A True Beauty
Getty | Tim Graham

Princess Diana's Style: A True Beauty

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.