When Prince Harry turned 36 in 2020, it was an equally celebratory and reflective moment for the newly independent royal. At age 36, his beloved mother Princess Diana died in a tragic car accident involving paparazzi, taking her from young sons Prince William and Harry far too soon. A doting mother, Diana was often seen bonding with young William and Harry, her two beloved boys with Prince Charles, and while Diana’s time as a royal may have been complicated, marked by media scandals and her ultimate divorce from Charles in 1996, her legacy as a mother is not. On this day, we’re honoring Diana’s best moments as a mom, as Harry will always remember her: from ski trips to water slides, first days of school, and more photos of Diana and the boys that we’ll never forget.
From his decision to step back from the royal family with Meghan Markle to his dedication to carrying on her charity work in Lesotho and beyond, it’s clear how much Harry has been influenced by Diana’s own path as a royal. And as he and William have taken on fatherhood, they’ve only been more reminded of aspects of their childhood with Diana that they’d like to carry on.
For William, that’s meant raising George, Charlotte, and Louis in Kensington Palace, where he and young Harry grew up with Diana, while for Harry, that’s meant raising Archie out of the public eye and giving him as much normalcy as possible, another goal of Diana’s throughout. Looking back on these photos of the three of them, we know Diana would be so proud of both her boys — and hope that, no matter what their differences, they’ll always find their way back to this close bond as brothers.
Harry and William have have, in many ways, devoted their legacies to ensuring Diana’s effect on the royal family would not be forgotten. These photos will remind you just how close Diana was with both her boys — we recommend getting out the tissues now.
A version of this article was originally published in August 2020.
Diana With Harry & William & Their Friends at Necker Island
This snapshot of Diana being buried in the sand by her sons Prince William and Prince Harry, along with their friends at Necker Island is the sweetest moment we’ve ever seen!
Diana & Harry Chilling at Highgrove House
Princess Diana was so happy while holding onto Prince Harry at their country home in Highgrove.
Skiing Mother-Son Trio
When Princess Diana was around her kids, it was all smiles, especially during this skiiing trip to Austria in 1993.
Diana & William Walk Home From Lunch
This 1997 pic was taken just 10 days before Diana’s tragic accident. She and 15-year-old William share a laugh on their walk home from a Chelsea restaurant.
Family Outing to Head of State Ceremony
Diana leans over to talk to her boys in this 1995 photo. We’re very curious what Harry’s grinning about on the right!
Diana & the Boys at Twickenham
This 1995 photo shows Diana and her two boys at Twickenham, a suburb of London.
Diana Drops the Boys at School
Though Diana and Charles had separated by this point, they still got together for the boys’ big days.
Royal Family Portrait
One of the few royal family portraits featuring this particular group, the photo shows William front and center, with mom Diana and brother Harry to the left.
William Signs the Eton Register
In 1995, William signed the register at Eton College, while proud parents Diana and Charles looked on. Harry rounds out the crew in a sweet suit and tie.
Diana Takes Her Boys to the Royal Tournament
This 1995 snap features William, Harry and an unnamed friend of Harry’s — along with a watchful (and very chic!) Diana to the left.
Diana & the Boys on a Ride at Alton Towers
More rides for Diana, William and Harry! This time, Diana had their friends come along for a ride at Alton Towers.
William’s First Day of School!
In 1995, William began at Eton College. This family photo was taken one day before his tenure at the school began.
Diana Celebrates V-J Day with William & Harry
This 1995 photo shows Diana with her two sons at the Queen Victoria Memorial. And Harry appears to be getting a bit antsy about the time!
Greeting the Public in Norfolk
This 1994 photo shows the royal family strolling past the public in Sandringham. We’re loving Diana’s hat, and look! William’s growing up so quickly…
Queen Elizabeth Takes Diana & William For a Ride
On William’s carriage ride with the Queen, we see a young Royal Majesty perfecting a graceful wave while the future king looks bashfully on.
Diana & Harry at the British Grand Prix
Even with sunglasses, you can see the love in Diana’s eyes in this 1994 photo. And Harry seems to be having an excellent time at the Grand Prix.
Wedding Rehearsal Time!
This 1989 snap shows Diana leading Harry and William to rehearsals for the wedding between Charles Spencer and Victoria Lockwood.
The Water Rides Continue!
It’s not just Harry who loves a water park! William gets in on the fun of this log ride too, and it looks like the whole family can’t help but grin.
Horse-Drawn Carriage Through Austria
Diana and her boys continue the Austria ski vacation with a horse-drawn carriage — and Diana and Will share a sweet look.
Family Ski Trip to Austria
Have we mentioned that they love to ski? Diana rests with her bundled-up boys on a skiing holiday in Austria, 1993.
Diana & Harry Go Down a Water Slide
Young Harry loved a good waterpark — and we know this because there are so many photos of the very game Diana hopping on a ride with him.
A Royal Trip to Windsor
This 1992 snap shows William and Harry all dressed up (if looking quite shy!) at Windsor. Diana is grinning down at her youngest.
Diana & Harry at Thorpe Park
This 1992 photo shows Diana placing a hand on Harry’s shoulder (then age 8). Diana’s smile and Harry’s copper hair are our favorite parts of this scene.
Diana & the Boys See a Rugby Match
Doesn’t that look on Diana’s face just melt your heart? This 1992 photo shows a family outing to the Wales v. France Rugby Union match.
Diana & Her Boys Hit the Slopes!
Diana loved to ski, and taught her boys from a young age. This 1991 photo shows Di and her boys riding up a chair lift.
Royal Family Waves Goodbye to Toronto
All aboard the Yacht Britannia! This 1991 photo shows Charles, Diana, William and Harry waving goodbye as they leave Toronto.
Diana & William at the International Horse Show
This 1990 Pic shows 8-year-old Wiliam touching mom Diana’s face, and it’s unbelievably sweet.
Diana Brings the Boys to the Queen’s Medical Center
This 1990 photo shows Diana, William and Harry heading into the Queen’s Medical Center to visit dad Charles, who injured his arm in a polo accident.
Carriage Ride with the Queen
Once again, these photos are giving us major 2019 vibes, given how similar the pics of Meghan Markle at this year’s event were. But how adorable is Harry’s little wave?
Young William & Harry at Trooping the Color
Remind you of anything? Perhaps these now-famous 2019 Trooping the Color photos of Prince Louis? Here’s the 1989 version, featuring all the same royals (for the most part), but 20 years younger.
Family Bike Ride!
This 1989 snap shows the family on vacation once again, this time in the Scilly Isles.
Harry Gets Wacky at Trooping the Color
The 1988 Trooping the Color shows Prince Harry getting a little goofy — and mom Diana appears to be having a stern word! We’re seeing a lot of resemblance between young Harry and young Princess Charlotte…
Harry & William Meet Their Baby Cousin Princess Beatrice
In 1988, Diana took her sons to the hospital to meet their newborn cousin: Princess Beatrice.
Harry & Will Play Dress-Up!
This adorable 1987 pic documents a stop at the British Transport Police — where Harry and William were clearly swiftly outfitted with helmets.
Harry Is Wowed by Trooping the Color
Little Harry is only 2 years old at the 1986 Trooping the Color, and while William waves confidently, Harry seems downright overwhelmed.
Diana & Her Boys Venture Out
On that same holiday in Majorca, Diana posed with her two boys on the steps — and it looks like the heat is getting to young Will.
Harry & William Rock Their Best Outfits Yet
Another photo from this 1987 Mallorca trip has us enraptured with Harry and William’s vacation style. Those overalls!!!
Harry & William Make a New Dog Friend
The Prince and Princess of Wales would often vacation alongside Diana, Charles, and the boys — but it looks like Harry is too enamored with his furry friend to notice.
Princess Diana Cuddles Prince Harry
One of the sweetest, and arguably best known photos of Princess Diana and Prince Harry, is this snapshot of the Princess of Wales cuddling her little boy during their trip to Majorca.
The Royal Family Takes Majorca
Harry is still so very tiny in this 1986 photo, which pictures the whole family at Maribend Palace in Spain.
Yacht Trip to Venice
In 1985, the family took a trip to Venice on the Royal Yacht Britannia. And it looks like Diana is loving young Will’s antics.
Diana & the Family Welcome Baby Harry
This 1984 snap shows newborn Harry posing with the rest of his family for this official royal photo.
Baby William Is Six Months Old
This 1982 photo shows William when he was just a bouncing baby boy.
St. Paul’s Cathedral
Diana’s two young sons wore their sharpest suits for this outing to St. Paul’s Cathedral.
‘Hook’ Premiere
With all those cameras snapping, Diana and her boys still look in their own little world.
Prince Harry Arrives To School
Upon arriving to school, Prince Harry was more than ready to make introductions to his new teacher. His mother, Princess Diana, couldn’t help but smile while watching her son reach out his hand.
Prince Harry On His First Day Of School
In this photo from September 1987, Princess Diana leads Prince Harry, who was only 3 years old, by the hand to his first day at a kindergarten in Notting Hill. Prince Charles was there too, holding Prince William’s hand as they saw Harry off.
Diana Goes In For A Hug
Princess Diana was always so affectionate with her two boys. In this photo, the late Princess of Wales is reunited with Prince William, center, and Harry, right, as she arrives aboard HMS Brittania in Toronto Harbor on Oct. 25, 1991.
Harry, William, & Diana Take A Boat Ride
Back in October 1991, Princess Diana took sons Harry and William on a ride with the Maid of Mist in Niagara Falls. Both young Princes were under the age of 10 at this time.
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