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Remembering Princess Diana on her birthday, we look back at her most stylish moments

Diana, during a visit to Footscray Park in Melbourne on January 27, 1988

Princess Diana would likely have celebrated her 56th birthday on July 1, had she not died in a car crash in Paris on August 31, 1997. While speculation about the reasons for her death has continued unabated since her death, numerous books, documentaries and interviews have long tried to unearth secrets about the private life of a princess whose looks, style and ability to inspire common folk everywhere ensured that every move and utterance captivated millions around the world. As we approach the 20th anniversary of her death, we look back at some of those highlights.

The Prince and Princess of Wales at a British Embassy dinner in Washington, on a visit to the United States.

White elegance

1981 – “Going in Lady Diana Spencer, coming out the Princess of Wales”

Her story begins here. Crowds of 600,000 people filled the streets of London and an estimated 750 million global audience watched the wedding ceremony on television. On July 29, 1981, the 20-year-old Diana Spencer walked down the aisle of St Paul’s Cathedral to marry Charles, Prince of Wales. Designed by David Emanuel and his former wife Elizabeth, Diana’s off-white wedding gown had voluminous sleeves, 10,000 pearls and a 25-foot train.

Marrying Charles at St Paul’s Cathedral

David recalled, “She was going in Lady Diana Spencer, she’s coming out the Princess of Wales, so this dress had to be young and sweet, but it also had to be glam because she was going to be a royal princess. She couldn’t do a quiet-looking, low-key little gown.” Obviously, the design duo made a massive success. Diana’s wedding look became a look for the ages.

1988 – One of Diana’s favourite dresses

This oyster duchesse-satin dress with a bodice and bolero embroidered by Hurel, the renowned hand embroidery house, was one of the favourite dresses of the Princess designed by Victor Edelstein. She wore it at a banquet in the Élysée Palace in Paris during the official visit with Charles in 1988. She paired the dress with the iconic Cambridge Lover’s Knot tiara – a wedding present from the Queen. The delicate dress showed off Diana’s elegant and aristocratic side.

The outfit was among Diana’s favourites

1989 – The “Elvis dress”

In 1989, Charles and Diana were invited to officiate the opening ceremony of the Hong Kong Cultural Centre. That night, Diana wore an outfit created by British designer Catherine Walker who was inspired by the Elizabethan ruff and created the distinctive sequin- and pearl- encrusted jacket. However, the dress came to known by the press as “Elvis dress” because of the similarities to Presley’s Las Vegas ensembles.

Diana wore the dress with the Cambridge Lover’s Knot tiara. The dress sold at a charity auction in 1997 for US$151,000

To raise fund for the Aids and cancer charities, Diana donated some of her outfits, including the “Elvis dress”, to Christie’s charity auction in 1997. The “Elvis dress” was bought by The Franklin Mint, which donated it to London’s Victoria & Albert Museum in 2005.

Charles and Diana at the Hong Kong Philharmonic Orchestra's performance to open the Cultural Centre in Tsim Sha Tsui in November 1989.

Vivid red

1986 – The rising sun

To honour her Japanese hosts, Diana wore a red polka dot dress symbolising the Japanese flag and wore it with a red boater when she flew into Kyoto for an official visit with Charles. She also tried on a kimono during the Nijo Castle tour, showing an entirely different style of a British princess.

Diana visited Japan in 1986

1986 – The sporty royal

Diana accessorised her fuchsia pink ski-suit with a stylish braided headband and gold hood earrings during a family holiday to Klosters, Switzerland. Who says you can’t be chic and stylish while hitting the slopes with your skis and poles?

Diana in a ski-suit during a family trip to Switzerland

1995 – Versace pink lady

Diana was required to wear British designers. However, a year before the divorce from Charles in 1996, she called on Gianni Versace for the Jacqueline Kennedy Onassis-inspired double-breasted pink suit, while the pillbox hat was from Philip Somerville. She confidently wore the set while inspecting the troops at Howe Barracks in Canterbury.

Versace double-breasted pink suit

Mellow Yellow

1983 – Belle of the ball

We spotted two gorgeous yellow outfits on Diana in 1983.

In March, when Diana was at Government House in Canberra, Australia, she wore a drop-waist style, V-necked yellow-gold silk taffeta designed by Murray Arbeid. She wore it several times that year during the trips to New Zealand and Canada, with various luxury jewellery.

The yellow-gold silk taffeta was paired with the Spencer Tiara and the Saudi sapphire pendant
The Spencer Tiara, Diana’s wedding crown

The Princess was a genuine hat lover and with her height, she looked good in any kind of hat. In April 1983, she wore a veil yellow hat by John Boyd, one of London’s most respected milliners, to the Maori Festival at Waitangi,Chatham Islands during the Royal Tour of New Zealand.

Charles and Diana at the Maori Festival in New Zealand in 1983

1987 – the elfin-like Princess

John Boyd was not the only designer to create a hat for the princess. The late milliner, Philip Somerville, had adorned members of various European royal families. In 1987, when Diana visited Berlin, she paired her yellow and back woollen coat in blanket checks from Escada with a turban hat by Somerville. Her fondness to deviate from being prim and proper won many admirers.

Diana in Berlin

Keen on green

1985 – the emerald choker

Diana had a lengthy collection of jewels. As one of the wedding gifts from the Queen, the emerald and diamond choker were worn as a tiara when she attended a ball at the Southern Cross Hotel in Melbourne. All eyes were on Diana when she glided across the dance floor with Charles.

The emerald choker was made for Queen Mary by Garrard in 1921, and inherited by the Queen in 1953

You may ask whether the Princess had to return the jewels after their divorce? Diana was allowed to keep all the jewels given by the Queen, on condition that she wouldn’t lend or sell them. The jewels all returned to the royal family after her death.

1992 – The humble goddess

When in Rome, do as the Romans do. Diana covered her head with a scarf when she admired the Al-Azhar Mosque in Cairo in 1992. She wore a calf-length pale green silk dress and left her feet bare.

Diana covered her head with a scarf on a visit to Al-Azhar Mosque in Cairo in 1992

Royal blue

1981 – The royal engagement

The couple announced their engagement in Buckingham Palace in 1981. This time, the attention of the world was not on the blue outfit that Diana was wearing when they met the press, but on the sapphire engagement ring. The stunning piece comprises 14 solitaire diamonds surrounding a 12-ct oval blue Ceylon sapphire set in 18-ct white gold.

Charles and Diana announce their engagement at Buckingham Palace in 1981

The Dutchess of Cambridge inherited the ring when she got engaged to Prince William in 2010, as the Prince wanted to make sure that her mother “didn’t miss out on the excitement”.

1987 – The “Travolta dress”

There is no way you can forget this dress. Designed by Victor Edelstein for her state visit to the United States to meet Ronald and Nancy Reagan, the off-the-shoulder ink-blue velvet gown was widely known as the “Travolta dress” as Diana danced at the White House with film star John Travolta.

Dancing with John Travolta at the White House in 1987

“That was one of the highlights of my life, so that’s probably the best moment of the eighties,” Travolta recalls. The dress sold for US$222,500 at Christie’s charity auction in New York City in 1997.

Balmy violet

1988 – Flower power

Diana was resplendent in a sari-style ball dress in fuchsia and purple silk chiffon during a Royal visit to Thailand. The backless evening dress was complemented by the Princess hair, adorned with purple and white orchids, like a Thai airline hostess.

The sari-style dress
Christie’s chairman Charles Hindlip gestures during the auction of Diana’s former sari-style ball dress in New York City. Proceeds from the evening, at which 80 of Diana’s old dresses were auctioned, were donated to charity. Photo: AFP

1989, 1992 – Thrifty princess

In 1989, the President of Nigeria, Ibrahim Babangida, made a state visit to Britain and Diana welcomed him with her purple beaded ball gown from Catherine Walker. Three years later, Diana appeared at an official banquet in South Korea with the lower part of the dress altered into a narrow skirt. Her Spencer tiara completed both looks.

Diana wore the same dress in Britain in 1989 (left) and South Korea three years later

Daring black

1985 – Meeting the pope

After giving birth to Prince William in 1982 and Prince Harry in 1984, Diana met Pope John Paul II at the Vatican in April 1985. Protocol requires women to wear long black dresses with sleeves and mantillas. Diana was no exception. Besides wearing a calf-length black lace dress with a veil made of the same fabric, Diana also put on the gloves, as requested by the Pope.

Charles and Diana meet the Pope at The Vatican in 1985
The Pope requested that Diana wear gloves

1994 – The “revenge dress”

On the night that Charles confessed to having an affair with Camilla Parker Bowles, now the Duchess of Cornwall, Diana donned this figure-hugging black silk dress to the Serpentine Gallery summer party. That’s how the dress got its name.

The “revenge dress”

1994 – The dandy lady

Forget those gowns and dresses worn to official occasions and look at Diana’s casual yet classy daily outfits. Gold elephants embroidered on the tie and around the cuffs and belts of Escada, she wore one hurrying to the St Mary’s hospital to meet her newborn nephew. In 1995, Diana gifted it to the daughters of a friend so that their father could wear it to a job interview. The tie later netted £3,800 at an auction in 2013.

Looking every inch the gentleman

We’re celebrating Diana’s birthday by looking back at her most iconic looks, from the 25-foot wedding train in 1981 to her ‘revenge dress’ in 1994