How Princess Diana became a fashion icon

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In the two decades since her death, Diana, Princess of Wales, has ascended to the pantheon of the best-dressed women in history, Eleri Lynn, curator of "Diana: Her Fashion Story," which opens February 24 at Kensington Palace told Vanity Fair on a recent phone call. "She is stepping into that same sort of space as an Audrey Hepburn or Jackie Kennedy," said Lynn, "a fashion icon whose style is so emulated and so loved, really."

How did she do it? The exhibition, staged in the galleries adjacent to the royal apartment Diana called home, follows the princess's style evolution, from the feather-haired "Sloane Ranger" fiancé of Prince Charles in pie-crust blouses and pastel ruffles whom the press nicknamed "Shy Di," to the sleek and regal woman whose confident stride in embellished gowns and body-con velvet made her one of the most-photographed women in the world.

SEE MORE: Princess Diana's style

41 PHOTOS
Princess Diana Style Transformation
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Princess Diana Style Transformation

1962

Lady Diana Spencer, later the wife of Prince Charles, on her first birthday at Park House, Sandringham.

1963

A very young Diana in a fancy pram.

1963

Lady Di at age 2.

1965

Young Lady Diana in a buttoned up dark coat.

1969

Lady Diana at age 8, wearing a matching dress and headband.

1970

Diana on holiday with her family, causal in a sweater and jeans.

1971

Diana let her hair grow long during her youth, here age 10 in a wide-brimmed black hat.

1980

Diana always had a passion for children, here at 19 working as a Nursery Assistant at a Kindergarten school.

1981

Diana and Charles pose on the day of their engagement, showing off her diamond and sapphire engagement ring.

1981

Diana was stunning on her wedding day, with the most glamorous dress and bouquet -- truly fit for a Princess.

1981

The royal couple during their honeymoon in Scotland.

1981

Diana attended an exhibition at the Victoria and Albert Museum, in a dress designed by Bellville Sassoon.

1982

Princess Diana, pregnant and glowing at a Polo match in Windsor.

1982

The Prince and Princess visit Wales, Diana wearing a suede beret by John Boyd and a coatdress by Arabella Pollen.

1983

Diana was a vision in yellow as she and Charles visited a school in Alice Springs, Australia.

1983

We're loving the pops of pink in Diana's outfit, here while watching Charles play Polo.

1984

Diana talks with Prince Charles, who is on horseback, at a Polo match.

1984

Diana is pretty in pink while attending the ballet Swan Lake.

1985

Diana and a tiny Prince William leaving the Royal Yacht, the Princess in a belted plaid jacket.

1985

Diana laughs with Nancy Reagan, the two ladies looking radiant in hues of red and white.

1986

Diana rests her chin in her hands on the steps of her home at Highgrove.

1986

Diana at a desert picnic in Saudi Arabia, wearing a purple and white outfit by Catherine Walker.

1987

Diana attended Cannes Film Festival, wearing a stunning ice blue gown by Catherine Walker.

1987

Diana was stunning at an evening function during a visit to Germany, wearing a gown by Victor Edelstein.

1988

Princess Diana during a visit to Melbourne.

1988

Diana and Wills at a polo club, the Princess casually dressed in a blazer with the British Lung Foundation logo on the front of her t-shirt.

1989

Diana looked radiant in red and purple while in Hong Kong, the outfit designed by Catherine Walker.

1989

During her visit to Hong Kong, Diana wore this stunning tiara and white dress, later known as the "Elvis Dress."

1990

The Princess of Wales in mint on an official visit to Hungary.

1990

Diana and her boys, attending a church service.  Diana wore a pink and purple suit by Catherine Walker.

1991

Diana wears her favorite designer once again, Catherine Walker, during an official visit in Brazil.

1991

Diana wore this white dress and black jacket designed by Catherine Walker during a visit to Salisbury.

1992

Diana was stunning at a banquet in Seoul, wearing the Spencer family tiara and a gown by Catherine Walker.

1993

Diana looked lovely in this pastel suit, crouching down to speak with a young boy.

1994

Lord Palumbo greets Princess Diana, wearing a short black cocktail dress designed by Christina Stambolian, as she atttends a gala.

1995

Diana visited army barracks, wearing a Versace suit and a hat by Philip Somerville.

1996

The Princess of Wales was gorgeous in this royal purple gown during a visit to Chicago.

1996

Diana visited Washington, dazzling the entire country in this lovely white gown.

1997

Diana was lovely in this pale blue cocktail dress by Catherine Walker, attending a charity reception.

1997

Diana, Princess of Wales, was radiant in red during another visit to Washington, D.C.

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What really set Diana apart was her ability to communicate with her clothing, Lynn explained. "It is very surprising how little footage there exists of the Princess actually speaking. We all have a sense of what we think she was like, and yet so much of it comes from still photographs, and a large part of that [idea] is communicated through the different clothes that she wore."

Diana developed a "very glamorous regal style" for overseas trips, for example, that paid homage to the host nation. She wore a dress emblazoned with gold falcons, an emblem of Saudi Arabia, during a trip to that country. This fashion diplomacy clearly reverberates in the legacies of Kate Middleton and Michelle Obama, for example, who often wear clothing that salutes to their guests' home countries.

And Diana had an almost uncanny sense for how her clothing might enhance her physical presence, epitomized by what the Princess herself deemed her "caring wardrobe." These were ensembles for the philanthropic visits that cemented her reputation as a world-class humanitarian and a woman of deep compassion. "Cheerful, colorful clothes, because she wanted to convey approachability and warmth," Lynn said. "She didn't wear gloves because she liked to hold people's hands. She would sometimes wear chunky jewelry so that children could play with it, and she never wore hats to children's hospitals after a while, because she said you couldn't cuddle a child in a hat."

Related: Princess Diana's life in photos:

74 PHOTOS
Princess Diana's life in photos
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Princess Diana's life in photos
Princess Diana wearing a tiara and diamond necklace on an official visit to Australia, April 12th 1983. (Photo by Tim Graham/Getty Images)
UNITED KINGDOM - JULY 01: An informal study of Prince CHARLES, the Prince of Wales, and Lady Diana SPENCER, whose wedding will take place at Saint-Paul's Cathedral, London on 29th July 1981. (Photo by Keystone-France/Gamma-Keystone via Getty Images)
LONDON - JULY 29: (FILE PHOTO) Prince Charles, Prince of Wales and Diana, Princess of Wales leave St. Paul's Cathedral following their wedding July 29, 1981 in London, England. (Photo by Anwar Hussein/Getty Images)
LONDON - JULY 29: Diana, Princess of Wales and Prince Charles ride in a carriage after their wedding at St. Paul's Cathedral July 29, 1981 in London, England. (Photo by Anwar Hussein/WireImage)
Prince Charles and Diana, Princess of Wales (1961 - 1997) pose together during their honeymoon in Balmoral, Scotland, 19th August 1981. (Photo by Serge Lemoine/Getty Images)
Princess Diana wearing a Jasper Conran suit during a visit to a community centre in Brixton, October 1983. (Photo by Princess Diana Archive/Getty Images)
PARIS, FRANCE: Britain's Princess Diana arrived in Paris Friday, 13 November, 1992, on a private three day visit she is making without her husband, Prince Charles. (Photo credit should read JOEL ROBINE/AFP/Getty Images)
HONG KONG, HONG KONG: Britain's Princess Diana stands with tennis players Michael Chang of the US (L) and Sweden's Jonas Bjorkman during the awards ceremony at the Hong Kong Open 23 April. Princess Diana, on a private visit to Hong Kong, watched as Chang defeated Bjorkman 6-3, 6-1 to win the tournament. AFP PHOTO (Photo credit should read EMMANUEL DUNAND/AFP/Getty Images)
The Princess of Wales visits Chinatown in Liverpool, April 1982. She is pregnant with Prince William, and wearing a pink wool maternity coat by Bellville Sassoon and a hat by John Boyd. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)
WINDSOR, UNITED KINGDOM - JUNE 06: Princess Diana At Polo, Just Two Weeks Before The Birth Of Her First Child, Prince William. Wearing A Maternity Dress Designed By Fashion Designer Catherine Walker She Is Walking With Sarah Ferguson. (Photo by Tim Graham/Getty Images)
LONDON - JUNE 22: New born Prince William with Diana, Princess of Wales and Prince Charles leave St. Mary's hospital on June 22, 1982 in Paddington, London, England,. He was born in the Lindo Wing of the hospital on June 21. (Photo by David Levenson/Getty Images)
LONDON, UNITED KINGDOM - FEBRUARY 01: Princess Diana Holding Her Baby Son, Prince William, At Kensington Palace. (Photo by Tim Graham/Getty Images)
NEW ZEALAND - APRIL 18: Princess Diana And Prince William In New Zealand. (Photo by Tim Graham/Getty Images)
(FILES) This picture taken 17 June 1997 shows Diana, Princess of Wales, a key volunteer of the British Red Cross Landmine Campaign at Red Cross headquarters in Washington DC. Princess Diana may have survived her fatal Paris car crash in 1997 if French medical staff had not wasted precious time, a leading British surgeon indicated at her inquest 19 November 2007. AFP PHOTO/FILES/Jamal (Photo credit should read JAMAL A. WILSON/AFP/Getty Images)
The Prince and Princess of Wales visit Barmouth in Wales, November 1982. She wears a suede beret by John Boyd and a coatdress by Arabella Pollen. (Photo by Terry Fincher/Princess Diana Archive/Getty Images)
The Princess of Wales visits University College Hospital in London, December 1982. She wears a John Boyd hat and a velvet suit by Caroline Charles. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)
LONDON, UNITED KINGDOM - FEBRUARY 01: Princess Diana And Prince Charles With Prince William And His Koala Bear Toy At Kensington Palace (Photo by Tim Graham/Getty Images)
Princess Diana (1961 - 1997) at the School of the Air, in Alice Springs, Australia, 30th March 1983. She is wearing a dress by Jan van Velden. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)
AYERS ROCK, AUSTRALIA - MARCH 21: Prince Charles, The Prince Of Wales And Diana, Princess Of Wales Standing In Front Of Ayers Rock During Their Official Tour Of Australia (Photo by Tim Graham/Getty Images)
NEW ZEALAND - APRIL 18: Princess Diana During A Visit To New Zealand Wearing A Dress Designed By Fashion Designer Donald Campbell (Photo by Tim Graham/Getty Images)
MANUKAU - APRIL 19: Diana Princess of Wales meets firemen during a visit to Manukau, near Auckland, New Zealand during the Royal Tour of New Zealand on April 19, 1983. Princess Diana wore a suit designed by Jan Van Velden, with a hat by John Boyd. (Photo by David Levenson/Getty Images)
CANADA - JUNE 23: Princess Diana in Edmonton during an official visit of Canada (Photo by Tim Graham/Getty Images)
Princess Diana (1961 - 1997) leaving St Mary's Hospital, London with her new-born son Prince Harry, September 1984. She is wearing a red coat by Jan van Velden. (Photo by Terry Fincher/Princess Diana Archive/Getty Images)
VENICE, ITALY - MAY 5: (FILE PHOTO) (L-R) Diana the Princess of Wales holds her son Harry, whilst looking at Prince William held by his father Prince Charles on May 5, 1985 in Venice, Italy. Prince William will celebrate his 21st birthday on June 21, 2003. (Photo by Georges de Keerle/Getty Images) On July 1st Diana, Princess Of Wales would have celebrated her 50th Birthday Please refer to the following profile on Getty Images Archival for further imagery. http://www.gettyimages.co.uk/Search/Search.aspx?EventId=107811125&EditorialProduct=Archival For further images see also: Princess Diana: http://www.gettyimages.co.uk/Account/MediaBin/LightboxDetail.aspx?Id=17267941&MediaBinUserId=5317233 Following Diana's Death: http://www.gettyimages.co.uk/Account/MediaBin/LightboxDetail.aspx?Id=18894787&MediaBinUserId=5317233 Princess Diana - A Style Icon: http://www.gettyimages.co.uk/Account/MediaBin/LightboxDetail.aspx?Id=18253159&MediaBinUserId=5317233
LA SPEZIA, ITALY - APRIL 20: The Prince and Princess of Wales in La Spezia during a tour of Italy. (Photo by Tim Graham/Getty Images)
TWERTON ON AVON - MAY 31: Diana Princess of Wales meets girl guides outside the Poolemead centre for the Deaf on May 31, 1985 in Twerton on Avon, Bath, Avon. (Photo by David Levenson/Getty Images)
CANADA - JULY 01: Diana Princess of Wales celebrates her birthday in Canada (Photo by Tim Graham/Getty Images)
Princess Diana (1961 - 1997) inspects a guard of honour during a two-day visit to the 1st Battalion, the Royal Hampshire Regiment in Berlin, October 1985. She is wearing a pink and black suit by Victor Edelstein and a hat by Frederick Fox. (Photo by Lucy Levenson/Princess Diana Archive/Getty Images)
UNITED KINGDOM - OCTOBER 04: Diana, Princess of Wales with her sons, Prince William and Prince Harry, at the piano in Kensington Palace (Photo by Tim Graham/Getty Images)
KLOSTERS, SWITZERLAND - FEBRUARY 06: Prince Charles With Princess Diana On A Ski-ing Holiday Together. The Princess Is Wearing A Red 'head' Ski Suit And A Headband And She Is Holding A Pair Of 'dynamic' Skis. The Prince Is Wearing A Blue Ski Suit And Carrying A Pair Of 'k2' Skis. (Photo by Tim Graham/Getty Images)
VIENNA - APRIL 16: Diana, Princess of Wales, wearing a sapphire diamond and pearl necklace, attends a banquet on April 16, 1986 in Vienna, Austria (Photo by Anwar Hussein/Getty Images)
TETBURY, UNITED KINGDOM - JULY 18: Princess Diana Carries Prince Henry (harry) On Her Shoulders At Highgrove. (Photo by Tim Graham/Getty Images)
UNITED KINGDOM - AUGUST 22: PRINCESS DIANA ON BOARD HMS TRAFALGAR NUCLEAR SUBMARINE MEETING THE CREW DURING A VISIT TO THE NAVAL SUBMARINE BASE IN FASLANE IN THE FIRTH OF CLYDE, SCOTLAND (Photo by Tim Graham/Getty Images)
SANDHURST - APRIL 10: Diana, Princess of Wales wears a Catherine Walker white suit with drum majorette gold frogging and epaulettes and a graham smith hat for her visit to the Sandhurst Military Academy on April 10, 1987 in Sandhurst, England (Photo by Anwar Hussein/Getty Images)
Princess Diana and Prince Charles of Wales attending a Lionel Richie concert at Wembley Arena, London, November 7th 1987. (Photo by Dave Hogan/Getty Images)
The Prince And Princess Of Wales At A Prizegiving, At Polo, Smiths Lawn, Windsor. (Photo by Julian Parker/UK Press via Getty Images)
Diana, The Princess Of Wales, And Prince William, At A Polo Match, Smiths Lawn, Windsor. (Photo by Julian Parker/UK Press via Getty Images)
ABERDEEN, SCOTLAND - AUGUST 14: Princess Diana With Her Sons Prince William And Prince Harry At Aberdeen Airport. (Photo by Tim Graham/Getty Images)
MAJORCA, SPAIN - AUGUST 10: Diana, Princess of Wales with Prince Harry on holiday in Majorca, Spain on August 10, 1987. (Photo by Georges De Keerle/Getty Images)
Princess Diana (1961 - 1997) driving an armoured vehicle with the Royal Hampshire Regiment at Tidworth, Hampshire, 23rd June 1988. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)
CHAMBORD, FRANCE - NOVEMBER 09: Diana, Princess of Wales, wearing a white and blue lace and sequin evening coat-dress designed by Catherine Walker for a dinner at the Chateau de Chambord during her official visit to France. (Photo by Tim Graham/Getty Images)
The Princess of Wales at the museum in Kuwait City, March 1989. She is wearing a gold embroidered bedouin gown that was presented to her with a silver tea set to mark the occasion of her visit. (Photo by Jayne Fincher/Getty Images)
The Princess of Wales with her sons William and Harry on the chair lift during a skiing holiday in Lech, Austria, April 1991. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)
LONDON, ENGLAND - MARCH 7 Diana, Princess of Wales attends the Premiere of Dangerous Liaisons, in London's West End, on March 7, 1989 in London, United Kingdom. (Photo by Julian Parker/UK Press via Getty Images)
ABU DHABI, UNITED ARAB EMIRATES - MARCH 15: The Prince And Princess Of Wales attend a desert picnic on March 15, 1989 in Adu Dhab, United Arab Emirates. (Photo by Georges De Keerle/Getty Images)
BATH - MAY 30: (FILE PHOTO) Prince William, Diana, Princess of Wales, Prince Harry and Charles, Prince of Wales, attend the wedding of the Duke of Hussey's daughter in May, 1989 in Bath, England. (Photo by Anwar Hussein/Getty Images)
LONDON, UNITED KINGDOM - SEPTEMBER 11: Princess Diana With Her Sons Prince William And Prince Harry Standing On The Steps Of Wetherby School On The First Day For Prince Harry. (Photo by Tim Graham/Getty Images)
INDONESIA - NOVEMBER 05: The Princess Of Wales Playing Bowls At Sitanalia Leprosy Hospital In Indonesia (Photo by Tim Graham/Getty Images)
NIGERIA - JUNE 3: (FILE PHOTO) (PRINCESS DIANA RETROSPECTIVE 17 OF 22) The Princess of Wales speaks with Nigerians circa 1990 during a visit to Nigeria. Princess Diana, 36-years-old, died with her companion Dodi Fayed, 41-years-old, in a car crash August 31, 1997 in Paris, France. Fayed was the son of an Egyptian billionaire. (Photo by Georges De Keerle/Getty Images)
The Princess of Wales and the Queen Mother in an open-topped landau on their way to the Royal Ascot race meeting, June 1990. The Princess wears a Catherine Walker suit and a Philip Somerville hat. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)
The Princess of Wales walks amongst crowds of children waving flags during her visit to Cullompton in Devon, September 1990. She is wearing a Catherine Walker dress. (Photo by Terry Fincher/Princess Diana Archive/Getty Images)
WASHINGTON, UNITED STATES - OCTOBER 05: Princess Diana With Mrs Barbara Bush At The White House (Photo by TIM GRAHAM/Getty Images)
Diana, The Princess Of Wales Takes Her Sons, Prince'S William, And Harry Out On The Boat ' Maid Of The Mist ' To View Niagara Falls. (Photo by Julian Parker/UK Press via Getty Images)
LONDON, UNITED KINGDOM - NOVEMBER 18: Diana Princess of Wales attends the Premiere of Hot Shots, in London's West End, on November 18, 1991 in London, United Kingdom. (Photo by Julian Parker/UK Press via Getty Images)
The Princess of Wales (1961 - 1997) talks to children at the British school in Seoul during a visit to Korea, 1992. (Photo by Linda Grove/Getty Images)
INDIA - FEBRUARY 11: Diana Princess of Wales sits in front of the Taj Mahal during a visit to India (Photo by Tim Graham/Getty Images)
CALCUTTA;INDIA - FEBRUARY: Princess Diana the Princess of Wales holds hands with a nun at Mother Teresa's Hospice in Calcutta during her visit to India in February of 1992. (Photo by Anwar Hussein/Getty Images)
GIZA, EGYPT - MAY 12: Diana Princess of Wales visiting the Pyramids in Giza during an official tour of Egypt. (Photo by Tim Graham/Getty Images)
EGYPT - MAY 13: Diana, Princess of Wales in teh Alazhar Mosque, Cairo, Egypt (Photo by Tim Graham/Getty Images)
LONDON, ENGLAND - JUNE 13: Diana, Princess of Wales, Queen Elizabeth, The Queen Mother, and Prince Harry, attend the Trooping The Colour Ceremony on June 13, 1992 in London, United Kingdom. (Photo by Julian Parker/UK Press via Getty Images)
Princess Diana (1961 - 1997) on a skiing holiday in Lech, Austria, March 1993. (Photo by Jayne Fincher/Getty Images)
Princess Diana (1961 - 1997) meets local people during a field visit to Red Cross projects in the remote mountain villages of Nepal, 3rd March 1993. (Photo by Princess Diana Archive/Getty Images)
Diana Princess Of Wales, Prince William & Prince Harry Visit The 'Thorpe Park' Amusement Park. (Photo by Julian Parker/UK Press via Getty Images)
Princess Diana (1961 - 1997) during a visit to the Red Cross borehole project for refugees in Zimbabwe, July 1993. She is wearing a safari suit by Catherine Walker. (Photo by Jayne Fincher/Getty Images)
Princess Diana (1961 - 1997), Prince Harry, Prince William and Prince Charles at a parade in the Mall, London, during V.J. Day commemorations, August 1994. Diana is wearing a Tomasz Starzewski suit and a hat by Philip Somerville. (Photo by Terry Fincher/Getty Images)
UNITED KINGDOM - MAY 20: Princess Diana Reviewing The Troops Of The Princess Of Wales Regiment In Kent. The Princess Is Wearing A Pink Suit Designed By Versace. (Photo by Tim Graham/Getty Images)
Diana, Princess Of Wales Attends The Serpentine Gallery Summer Party. (Photo by Julian Parker/UK Press via Getty Images)
LONDON -OCTOBER 08: Diana, Princess of Wales laughs as she visits the London Lighthouse, the HIV/Aids charity, to help launch it's £1.5 million Capital Appeal on October 08, 1996 in London, England . (Photo by Anwar Hussein/Getty Images)
Diana, Princess of Wales at Costume Institute Gala at Metropolitan Museum of Art for a benefit ball. (Photo By: Richard Corkery/NY Daily News via Getty Images)
ANGOLA - JANUARY 15: Diana, Princess of Wales wearing protective body armour, visits a minefield being cleared by the chirty Halo in Huambo, Angola (Photo by Tim Graham/Getty Images)
WINDSOR, UNITED KINGDOM - MARCH 09: Official Portrait Of The Royal Family On The Day Of Prince William's Confirmation. Front Left To Right - Prince William, Princess Diana, Prince William, Prince Charles And The Queen. Back Left To Right - King Constantine, Lady Susan Hussey, Princess Alexandra, Duchess Of Westminster And Lord Romsey (Photo by Tim Graham Picture Library/Getty Images)
GREAT BRITAIN - JUNE 06: Diana, Princess of Wales crouching down to embrace a pupil at the Shri Swaminarayan Mandir in Neasden (Photo by Tim Graham/Getty Images)
Diana, The Princess Of Wales Visits Washington, Usa.Gala Dinner Held By The American Red Cross, To Raise Funds For Landmine Victims Around The World. . (Photo by Mark Cuthbert/UK Press via Getty Images)
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Even textiles were an opportunity for Diana to convey empathy: "if she was visiting hospitals for the blind, she would often wear velvet so that she would feel sort of warm and tactile," Lynn explained.

She was also deeply aware of how clothing might shape her public image: "One of her most famous gestures, which is to remove her gloves very conspicuously to hold hands with patients—you know she's using clothing and fashion in order to really hammer home that message."

It isn't simply Diana's standards for public dress that made her an icon, however, but the impressive evolution of her style. "What's amazing to me, when you first meet Lady Diana Spencer in the exhibition, you meet her in her debutante dress from 1979," Lynn noted, "and it's very frilly, very lacy, and very far removed from the fashion icon that she would become." In fact, the woman whose career would soon command hundreds of ensembles a year had just three items of clothing in her wardrobe at the time (the rest she borrowed from friends, fellow "Sloane Rangers" with whom she shared an apartment in London's posh Sloane Square and who populated the party pages of Tatler).

More: Prince George and Princess Charlotte's Cutest Moments

But Diana was a quick learner when it came to developing a uniform for her new royal role in the public eye, Lynn said: "You really see the frills and the ruffles of her early romantic style disappearing quite quickly, as she realized that didn't work very well for press photographs. It made her look cluttered. So around the 80s you see the silhouette sleek down, and all the decoration becomes surface embellishment." Gone were the gauzy pastel valences of the Bellville Sasson dress in which she famously snoozed at an event at the Victoria & Albert Museum while pregnant with Prince William; in were the form-fitting, even clingy, bodices of Catherine Walker and Victor Edelstein, and the embellished sheaths of Versace.

Diana had a knack for choosing pieces that suited her, rather than what seemed of the moment—a particular feat in the trend-driven 80s and 90s. "That's what sort of takes somebody above daily fashion," said Lynn, "and helps make them a fashion icon: they have that elegance that is theirs and doesn't move with the changes of fashion." A mermaid-teal sequin Catherine Walker dress with large shoulder pads looks of the 80s, yet it also echoes the golden age Hollywood costumier Adrien, or the emerald Versace dress Angelina Jolie wore to the 2011 Golden Globes.

SEE MORE: Kate and Diana's style

16 PHOTOS
Princess Diana and Duchess Middleton Style
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Princess Diana and Duchess Middleton Style

PRINCESS DIANA'S TAKE

The Prince and Princess of Wales leaving the Lindo Wing, at St. Mary's Hospital after the birth of their baby son, Prince William.

DUCHESS KATE'S TAKE

The Duke and Duchess of Cambridge leaving the Lindo Wing of St Mary's Hospital in London, with their newborn son Prince George of Cambridge, one of the ten best moments of the royal couple's five years of marriage.

YOUR TAKE

The Real Ahoy Dress in Dots, $79,99, Modcloth

PRINCESS DIANA'S TAKE

DUCHESS KATE'S TAKE

The Duchess Of Cambridge Attends 'A Night Of Heroes: The Sun Military Awards', Imperial War Museum, London.

(Photo by Mark Cuthbert/UK Press via Getty Images)

PRINCESS DIANA'S TAKE

YANDINA - APRIL 12: Diana Princess of Wales and Prince Charles visit Yandina Ginger Factory on April 12, 1983 in Queensland, Australia during the Royal Tour of Australia.

(Photo by David Levenson/Getty Images)

DUCHESS KATE'S TAKE

Catherine, Duchess of Cambridge and Prince William, Duke of Cambridge arrive at Calgary Airport on July 7, 2011 in Calgary, Canada.

(Photo by Chris Jackson/Getty Images)

YOUR TAKE

Yellow chiffon maxi wedding dress, $109-159, Etsy

PRINCESS DIANA'S TAKE

LEEDS, UNITED KINGDOM - MARCH 29: Princess Diana visiting Bristol during her pregnancy with her first son, Prince William. Diana is wearing a coat designed by Bellville Sassoon and a hat designed by milliner, John Boyd. 

(Photo by Tim Graham/Getty Images)

DUCHESS KATE'S TAKE

Catherine, Duchess of Cambridge laughs as she attends the St Patrick's Day parade at Mons Barracks on March 17, 2014 in Aldershot, England. Catherine, Duchess of Cambridge and Prince William, Duke of Cambridge visited the 1st Battalion Irish Guards to present the traditional sprigs of Shamrocks to the Officers and Guardsmen of the Regiment.

(Photo by Chris Jackson/Getty Images)

PRINCESS DIANA'S TAKE

EPSOM, UNITED KINGDOM - JUNE 04: Diana, Princess Of Wales With Prince Philip On Derby Day. Princess Diana Is Wearing A Polka Dot Day Dress Designed By Fashion Designer Victor Edelstein.

(Photo by Tim Graham/Getty Images)

DUCHESS KATE'S TAKE

The Duke of Cambridge, Prince William, The Duchess of Cambridge, Catherine Middleton and Prince Harry attend the inauguration, and make an official visit at Warner Bros, Leavesden Studio, London on April 26, 2013 in Watford, England.

(Photo by Julian Parker/UK Press via Getty Images)

YOUR TAKE

Belted Polka-Dot A-Line Dress, $89, Macy's

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Diana's whimsy with clothing is also finding new appreciation in a younger generation, who are celebrating her on the runway or on Instagram, whether twirling on John Travolta's arm in a midnight blue velvet Victor Edelstein at the White House or darting into the Harbour Club in spandex shorts and a Harvard sweatshirt. "She did clearly have fun with fashion," Lynn says, "and she took risks . . . and experimented with her style. She was the first member of the royal family to be photographed wearing trousers to evening events. But she often teamed that with tuxedo jackets and bowties—that's quite the bold, fun look that you don't necessarily expect of a princess."

But what has made her image even more powerful over time is that she truly knew what looked good on her, Lynn says, which gave her glamour a certain naturalness. "A lot of designers say that she had this look about her that she'd just sort of run in, and run her fingers through her hair," Lynn said, adding that designers also point to "an incredible presence and incredible charisma that lifted her above those seasonal changes."

That confidence in her appearance is what makes Diana, not just her wardrobe, iconic. "She had really sort of transcended fashion and achieved an incredible chic and elegance," said Lynn, such that "all you saw was her, and the clothes became secondary to her own presence and her work."

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