Princess Diana’s Most Memorable Outfits

Diana, Princess of Wales, will always be remembered for her philanthropy and her uncanny ability to stay relate-able even though she was a royal. But the People’s Princess also had a passion for fashion and always made an impact when the cameras were pointed towards her. From the frilly wedding gown to the infamous “Elvis dress” (see page 14) here are 15 of Princess Diana’s most memorable outfits.

1. Introducing: The ring

Lady Diana Spencer and Prince Charles following the announcement of their engagement | Tim Graham/Getty Images

The blue suit Diana wore when she and Prince Charles announced their engagement is easily one of her most memorable ensembles. The occasion also marks the first time the public got to see her now-infamous sapphire ring, which she displayed proudly in her engagement photos. (That ring, of course, has been passed on to Kate Middleton.)

Next: All the frills …

2. Engagement ensembles

Lady Diana Spencer on a walkabout at Broadlands during her engagement | Tim Graham/Getty Images

Many of Diana’s ensembles during her time as a royal — especially early on — featured a plethora of ruffles and frills, like this one she wore at Broadlands during her engagement. Although later it was revealed she dressed this way to fit in with royal family standards. Her personal style, which was much more streamlined, came out more after her divorce from Prince Charles.

Next: And if you thought that collar was frilly …

3. Wedding (dress) of the Century

Diana, Princess of Wales, wearing an Emanuel wedding dress, leaves St. Paul’s Cathedral with Prince Charles, Prince of Wales following their wedding on 29 July, 1981 in London, England | Anwar Hussein/Getty Images

The Princess of Wales was the talk of the town — the whole globe actually — when she married Prince Charles on July 29, 1981. Her large Emanuel wedding dress and gargantuan train were left to her sons, Prince William and Prince Harry, in her will.

Next: Not everything had ruffles …

4. Globetrotting in style

Prince Charles dozing for a few moments while Princess Diana watches a display of dancing in Fiji | Tim Graham/Getty Images

Traveling all over the world can be a grueling feat, but that doesn’t mean the royals can stop looking stylish. Diana rocked a sleek, warm-weather-friendly frock when she and Prince Charles made a quick trip to Fiji in the middle of visits to Australia and the United States.

Next: Speaking of visiting the States …

5. Her first trip to the USA

Prince Charles and Princess Diana meet President Ronald Reagan and First Lady Nancy Reagan at the White House on November 9, 1985 |Tim Graham/Getty Images

Princess Diana was noted as being “very charming” when she made her inaugural visit to the United States with Prince Charles to meet President Ronald Reagan and First Lady Nancy Reagan. Her sleek black dress became one of her most memorable outfits — in part because she was wearing it when she danced with John Travolta.

Next: Very regal …

6. Pretty in periwinkle

diana at the museum
Diana at the V&A Museum attending the ‘Splendours of the Gonzagas’ exhibition wearing a dress designed by fashion designers Bellville Sassoon | Tim Graham/Getty Images

Diana’s appearance at the Victoria & Albert Museum exhibit “Splendours of the Gonzagas” in 1981 is memorable for two reasons. The first, of course, was for the beautiful Bellville Sassoon dress she wore. The second was because she dozed off while sitting onstage.

Next: There was always something blue …

7. Attending fashion shows

The Princess of Wales arrives at the Guildhall in London for a fashion show, November 1982 | Jayne Fincher/Princess Diana Archive/Getty Images

Princess Diana’s passion for fashion was apparent in everything she wore — but especially when she attended fashion-focused events. One great example is when she attended a fashion show at Guildhall in London with her ladies-in-waiting, wearing a stunning blue Bruce Oldfield number.

Next: The little prince …

8. Introducing: Prince William

Newborn Prince William with Diana, Princess of Wales and Prince Charles leave St. Mary’s hospital on June 22, 1982, in Paddington, London, England |David Levenson/Getty Images

Diana’s first son, Prince William, was the first in the royal bloodline to be born at a hospital instead of at home. So naturally, there was press waiting outside of St. Mary’s Hospital to greet them. Her polka-dot frock instantly became memorable.

Next: Lady in red …

9. Introducing: Prince Harry

Princess Diana leaving St Mary’s Hospital, London with her new-born son, Prince Harry, 16th September 1984 |Terry Fincher/Princess Diana Archive/Getty Images

Princess Diana’s style evolved over her time in the spotlight to incorporate more statement jackets. This was evident when she emerged from St. Mary’s Hospital with newborn Prince Harry in 1984 wearing a stylish red Jan van Velden blazer.

Next: The fairest of them all …

10. The birthday girl

Diana attends a gala dinner at the Tate Gallery on her 36th birthday | Mark Cuthbert/UK Press via Getty Images

Diana’s 36th birthday celebration at London’s Tate Gallery in 1997 was her last before she tragically passed away. She was a year removed from her divorce from Prince Charles and was doing what she could to put her troubled married years behind her. She looked stunning in the process, donning a Chantilly lace gown by Jacques Azagury which the designer had given her as a birthday gift.

Next: Baring arms …

11. At the Cannes Film Festival

Diana, Princess of Wales, wearing a pale blue chiffon dress and matching stole by Catherine Walker | Anwar Hussein/Getty Images

Late fashion designer Catherine Walker was one of Diana’s go-tos for red carpet events and other big happenings. This included the ethereal sleeveless blue chiffon dress the Princess of Wales wore at the Cannes Film Festival in 1987.

Next: Hats off …

12. Attending the Ascot

Diana, Princess of Wales, and Sarah, Duchess of York, stroll through the Royal Enclosure at Royal Ascot races |David Levenson/Getty Images

When she wasn’t rocking a tiara, Diana could often be found wearing a variety of awesome hats. She was particularly keen to bright colors for balcony appearances or trips to the races — and the blue-and-yellow ensemble she wore at Royal Ascot in 1987 is definitely a standout.

Next: Looking beautiful even when abroad …

13. At the Elysee

Prince Charles and Diana, Princess of Wales, meet guests arriving at a dinner in November 1988, during the Royal Tour of France | David Levenson/Getty Images

Keeping up with royal duties, two children, and the stress of being in an unhappy marriage never dulled Diana’s sparkle. Here she’s seen with Prince Charles during a tour of France in 1988, looking regal as ever in a Victor Edelstein dress for dinner in the Elysee Palace in Paris.

Next: One of her most iconic outfits …

14. The ‘Elvis’ Dress

Diana, Princess of Wales wears a white Catherine Walker gown, known as the Elvis dress | Tim Graham/Getty Images

While the chiffon gown at the Cannes Film Festival was a hit, Catherine Walker’s beaded white gown with matching bolero may be even more iconic. Diana wore the frock, which she infamously dubbed her “Elvis dress”, to the British Fashion Awards at Royal Albert Hall in 1989.

Next: Last but not least …

15. Casual elegance

The Princess Of Wales with Princes William and Harry at the V-J Day 50th anniversary celebrations in London |Antony Jones/Julian Parker/UK Press via Getty Images

While many of Diana’s most memorable outfits were worn at royal engagements, she also made headlines for wearing more casual attire when hanging out with her sons. But the trio had a memorable fashion-forward family moment while attending the V-J Day 50th anniversary celebration in 1995, when Diana donned a clean-cut white dress suit and pearls.

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