Princess Diana was not only a beloved royal and humanitarian but also a devoted mother who cherished every moment with her sons, Prince William and Prince Harry. One of the ways she expressed this love was through fashion, often coordinating her outfits with theirs—sometimes subtly, sometimes boldly.
While Prince William found it embarrassing to be dressed like his younger brother, Harry seemed unfazed, happily embracing their matching ensembles. From playful stripes to elegant pastels, Diana and Harry’s coordinated looks remain some of the most heartwarming images in royal history.
In 1988, Diana and a young Prince Harry made a striking appearance at Trooping the Colour, dressed in coordinating mint green outfits. The late Princess wore a refined two-piece by Catherine Walker, featuring a sleek silhouette that radiated effortless elegance.
Her Philip Somerville hat, with its bold white trim, added a touch of regality, while pearl earrings and a delicate necklace completed the sophisticated look.
Harry, always full of charm, matched his mother in a jade green outfit, featuring adorable shorts with braces and a crisp white shirt. The duo's twinning moment was a testament to Diana’s careful attention to detail, ensuring that her son was just as stylish as she was for the grand royal event.
The summer of 1986 saw the royal family enjoying a sun-soaked getaway in Majorca, and Diana once again leaned into the mummy-and-me trend. The Princess of Wales stepped out in a stunning asymmetrical dress with diagonal stripes, capturing the effortless glamour that defined her style.
Harry, still a toddler at the time, was dressed in a simple but perfectly coordinated striped T-shirt. The images of the pair, both smiling in their relaxed yet stylish holiday attire, exude warmth and showcase Diana’s ability to turn everyday moments into picture-perfect memories.
Easter Sunday in 1989 saw Diana and Harry once again stepping out in complementary outfits, this time in shades of pink and burgundy. Diana made a statement in a raspberry-hued double-breasted coat with black lapels, paired with a bright pink polka-dot blouse and a dramatic wide-brimmed hat.
The bold color choices highlighted her fearless approach to fashion, making her stand out effortlessly among the royal crowd.
Harry, as always, was her perfect little companion, mirroring her style in a smart burgundy coat. His knee-high socks and polished leather brogues completed the charming ensemble, proving that Diana had an impeccable eye for mother-son coordination.
Casual yet classic, Diana and Harry proved that twinning wasn’t just for formal occasions. In one of their most relaxed and candid moments at Highgrove, the two were seen in crisp white tops—Diana in a chic, tailored version and Harry in a simple long-sleeved jersey.
What truly stole the show, however, was Harry’s candy cane-striped dungarees, adding a playful pop of color to their coordinated look. With his bright red suspenders and shiny shoes, the young prince looked every bit the stylish royal-in-the-making.
The moment captured the effortless bond between mother and son, a snapshot of Diana’s love and joy in raising her children.
The Buckingham Palace balcony is one of the most iconic settings for royal appearances, and in 1989, Diana and Harry once again showcased their flawless coordination. Diana was a vision in a pastel pink linen dress by Victor Edelstein, featuring a striped bow detail and elegant buttons running down the front.
Her signature pearl drop earrings and a grand saucer hat added an extra touch of royal grace.
Standing beside her, Harry looked every bit the miniature gentleman in a blush-colored shirt and a navy blazer. His crimson tie added a bold contrast, mirroring his mother’s polished yet playful style.
The moment, frozen in time through photographs, reflects the unique way Diana infused love and personality into her royal duties.
While the matching outfits made for adorable photographs, they also symbolized something deeper—Diana’s unwavering devotion to her sons. She never shied away from embracing her role as a mother, ensuring that Harry and William were raised with warmth, laughter, and as normal an upbringing as possible.
Her choice to coordinate with Harry, especially, reflected their close bond—one that remained strong throughout her life.
Even years after her passing, Prince Harry continues to honor his mother’s legacy, carrying forward her values of kindness, compassion, and a modern approach to royal life. And while he may no longer wear matching outfits with her, the memories of their twinning moments remain some of the most cherished in royal history.
