Princess Diana’s 10 sweet moments with William and Harry: From first day at school to holidaying in Spain

By Nabanita Pain
Published on : 05:10 PST, Jul 2, 2024

Princess Diana doted on her sons Prince William and Prince Harry and shared a close relationship with them until her death in 1997 (Tim Graham Photo Library via Getty Images)

A glimpse into Princess Diana's 10 most beautiful moments with William and Harry

Princess Diana's some of the sweetest moments with Harry and William (Tim Graham Photo Library via Getty Images) — Princess Diana shared a close bond with her sons Princes William and Harry (Tim Graham Photo Library via Getty Images)

Princess Diana's legacy is multifaceted, encompassing her role as the "People's Princess", her unwavering commitment to humanitarian causes, and her distinctive style sense. Perhaps her greatest fame came from becoming a mother to her two sons, Prince William and Prince Harry. Diana has had several of her cutest moments with Harry and William, from the thrill of starting school to having fun at theme parks. The royal mother-of-two raised her two young sons with a playful and encouraging style that seemed to bring out the best in them. Check out the 10 images below to witness some of their cutest moments together.

1. Prince William's first day of secondary school

Prince William with Diana, Princess of Wales and Prince Harry on the day he joined Eton in September 1995. (Photo by Anwar Hussein/WireImage) — Prince William with Princess Diana and Prince Harry on the day he joined Eton in September 1995 (Anwar Hussein/WireImage)

In 1995, Prince William became the first senior royal student to enroll at Berkshire, England's Eton College. In 1995, Princess Diana arrived at the famous Eton near Windsor in Berkshire with Prince William for his first day of secondary school, and she couldn't contain her excitement. Harry, who would later enroll as a student in 1998, per Woman and Home magazine, was with them.

2. Prince Harry's first day of primary school

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 Photo Library via Getty Images) — Princess Diana with Prince William and Prince Harry standing on the steps of Wetherby School on the first day for Prince Harry (Tim Graham Photo Library via Getty Images)

Princess Diana appeared to be brimming with pride on Prince Harry's first day of primary school in 1989—a sentiment that any parent can relate to. Diana's younger son gazed lovingly up at his elder brother, who was already a student, as they posed for pictures on the steps of London's Wetherby School. Their matching uniforms only served to highlight how adorable they were.

3. Prince William and Prince Harry's earliest photocalls

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 Photo Library via Getty Images) — Diana, Princess of Wales, with her sons, Prince William and Prince Harry, at the piano in Kensington Palace (Tim Graham Photo Library via Getty Images)

Philanthropist Diana always found time for her kids, whether it was teaching them how to play the piano at Kensington Palace or dressing them in matching red school uniforms for their first day of kindergarten. In 1985, Prince William and Prince Harry held one of their first joint photocalls at Kensington Palace. Princess Diana, their mother, taught the younger brothers how to play the piano while having the appearance of a devoted parent.

4. Princess Diana all smiles at theme park with Harry and William

Diana Princess Of Wales, Prince William & Prince Harry Visit The 'Thorpe Park' Amusement Park. (Photo by Antony Jones/UK Press via Getty Images) — Princess Diana, Prince William and Prince Harry visit the Thorpe Park Amusement Park (Antony Jones/UK Press via Getty Images)

Princess Diana made every effort to keep young William and Harry out of the spotlight and to maintain as much normalcy as possible in their upbringing, even if it meant completing the school run or taking them to a theme park for a treat. In 1993, Princess Diana didn't appear to mind getting drenched when riding a water attraction at Thorpe Park with her sons. The royal mother-of-two—who had split from Prince Charles the previous year—went out with William and Harry and it looked like they had a great time.

5. Prince Harry's mischief while attending Trooping the Color

LONDON, UNITED KINGDOM - JUNE 11: Prince Harry Sticking His Tongue Out Much To The Suprise Of His Mother, Princess Diana At Trooping The Colour With Prince William, Lady Gabriella Windsor And Lady Rose Windsor Watching From The Balcony Of Buckingham Palace (Photo by Tim Graham Photo Library via Getty Images) — Prince Harry sticking his tongue out much to the surprise of his mother, Princess Diana, at Trooping the Color with Prince William in 1988 (Tim Graham Photo Library via Getty Images)

As is customary for royal children, Prince Harry was seen playfully poking his tongue out while on the Buckingham Palace balcony as an alarmed Princess Diana looked on. The two were participating in Trooping the Color in 1988, standing next to Prince William, Lady Gabriella Windsor, and Lady Rose Windsor.

6. Vacationing in sunny Spain

Diana, Princess of Wales (1961 - 1997) with her sons William and Harry during a holiday with the Spanish royal family at the Marivent Palace in Palma de Mallorca, Spain, August 1987. (Photo by Terry Fincher/Princess Diana Archive/Getty Images) — Princess Diana with her sons William and Harry during a holiday with the Spanish royal family at the Marivent Palace in Palma de Mallorca, Spain, August 1987 (Terry Fincher/Princess Diana Archive/Getty Images)

In Palma de Mallorca, Spain, in 1987, Princess Diana was seen cuddling up with her infant sons while wearing a stylish yellow jumpsuit. The future King Charles and the three of them were vacationing at the invitation of the Spanish royal family, with Harry seeming to be adjusting to the warmer weather slightly better than William.

7. Princess Diana with her sons at official VJ Day

LONDON, UNITED KINGDOM - AUGUST 19: Princess Diana With Prince Harry & Prince William At A Parade To Commemorate The 50th Anniversary Of Vj Day Designer Of Diana's Suit - Tomasz Starzewski (please Check - People Magazine, 04/12/1999) (Photo by Tim Graham Photo Library via Getty Images) — Princess Diana with Prince Harry and Prince William at a parade to commemorate the 50th anniversary of VJ Day (Tim Graham Photo Library via Getty Images)

Princess Diana and her sons attended the official VJ Day 50th anniversary celebrations in London in 1995—one year prior to her divorce from Charles. William and Harry accompanied their mother, who looked stunning in a white striped skirt suit paired with pearls and a hat. It was one of Princess Diana's most memorable looks.

8. Twinning in matching outfits

Diana, Princess of Wales (1961 - 1997) arrives at Aberdeen airport in Scotland on the Royal Flight, with her sons Prince William and Prince Harry, 14th August 1989. They are spending the holidays in Balmoral. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images) — Princess Diana arrives at Aberdeen Airport in Scotland on the royal flight, with her sons Prince William and Prince Harry, on August 14, 1989 (Jayne Fincher/Princess Diana Archive/Getty Images)

Princess Diana was widely renowned for her sense of style, but her influence on Prince William and Prince Harry's childhood wardrobes is possibly less famous. Diana had a charming habit of dressing her young sons in matching outfits whenever feasible. In 1989, the two looked lovely on Aberdeen Airport's windswept runway wearing matching red jumpers and striped shorts.

9. Accompanying Prince William and Prince Harry in carriage

Diana, Princess of Wales (1961 - 1997) riding in a traditional sleigh with Prince William and Prince Harry during a skiing holiday in Lech, Austria, 30th March 1993. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images) — Princess Diana riding in a traditional sleigh with Prince William and Prince Harry during a skiing holiday in Lech, Austria, March 30, 1993 (Jayne Fincher/Princess Diana Archive/Getty Images)

Although Prince William and Prince Harry might not be as accustomed to riding in a carriage as others were, they appeared particularly happy to be utilizing it when on vacation in Lech, Austria in 1993. Princess Diana loved to ski in Lech, Austria, although the town might not have had an official royal family vacation house. The three of them could be seen smiling, curled up in their furs.

10. Princess Diana guiding her sons on royal trips

The Princess of Wales takes her sons William and Harry out on the boat 'Maid of the Mist' at Niagara Falls during a visit to Canada, October 1991. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images) — Princess Diana takes her sons William and Harry out on the boat 'Maid of the Mist' at Niagara Falls during a visit to Canada, in October 1991 (Jayne Fincher/Princess Diana Archive/Getty Images)

During some of her sons' first royal trips as young adults, Princess Diana was frequently spotted putting her young boys at ease. When Prince Harry visited Niagara Falls in 1991—his first official overseas engagement—she was seen putting a squeeze on his shoulders. Prince William, meantime, seemed to be receiving encouraging words.

Share this article: Princess Diana’s 10 sweet moments with William and Harry: From first day at school to holidaying in Spain