Princess Diana’s legacy is truly larger than life. Throughout her time at Kensington Palace and beyond, the Princess of Wales revolutionized what it meant to be royal, leading with her heart and earning the title of “the people’s princess” through her fearless, humanitarian approach to leadership, even in the face of extraordinary adversity. Her death shook the world, not just the United Kingdom.
Today would have been her milestone 65th birthday, and to honor her, we’ve rounded up some of her most iconic beauty moments. Because while breaking boundaries will forever be her greatest legacy, her status as a style icon is one that is also timelessly iconic.
July 1981: The Royal Wedding
We would be remiss not to kick off Princess Diana’s best looks with her wedding look. With her hair styled in her signature soft, feathered bob framing her face, a natural makeup look and her David and Elizabeth Emmanuel gown in tow, the Princess of Wales’ wedding ensemble is one that will forever go down in history.
February 1983: Kensington Palace
One of the earliest official headshots of Princess Diana, this stunning close-up taken at Kensington Palace showcases the princess’s early aesthetic: a perfectly coiffed bob, subtle eye makeup, extra rosy blush and a bare lip.
November 1985: The British Embassy
Taken during a dinner at the British Embassy in Washington, D.C., in November 1985, this close-up image of Princess Diana donning a lace gown and the Queen Mary tiara, a gift from the Queen, highlights the princess’s out-of-the-box beauty aesthetic. With a flush of blush across the face, a hint of silver eyeshadow on her lids, a coral glossy lip and what appears to be blue eyeliner on her waterline, this look highlights Princess Diana’s natural beauty and unconventional approach to fashion and style.
May 1988: Guards Polo Club
Even in her off-duty era, Princess Diana understood the assignment. Photographed at the Guards Polo Club in Windsor on May 2, 1988, the Princess of Wales paired her British Lung Foundation sweatshirt, a nod to her role as the charity’s patron, with jeans, boots, a baseball cap and hoop earrings for a look so beloved the original sweatshirt would go on to sell at auction for over $221,000. Bare-faced and effortlessly cool, it’s proof Diana’s off-duty glow was just as iconic as her red-carpet radiance.
November 1998: Armistice Day
Photographed here at a wreath laying ceremony on Armistice Day in November 1988, it’s clear that eye makeup was a key part of Princess Diana’s signature look. With the same eye-opening blue eyeliner on her waterline, this time paired with a thick line of black on her upper lid and a nude lip, the look is a moodier take on her classic style.
June 1994: The ‘Revenge Dress’
Arguably one of Princess Diana’s most iconic moments, her off-the-shoulder black Christina Stambolian gown worn to the Serpentine Gallery on June 29, 1994, was not just remarkable for its stark contrast from the typical dress of royals at the time, but it also made headlines for coinciding with the day Prince Charles admitted to adultery on national television, thus earning the ensemble the “revenge dress” title. Paired with her signature pixie cut tousled to perfection, a smoky eye and a glossy lip, Princess Diana’s look is just like her: bold, unapologetic and unforgettable.
November 1995: Cancer Research Gala
Another jaw-dropping moment, Princess Diana’s look for the Cancer Research Gala in 1995 highlights her transition to a more cropped, pixie style. Her sultry eye look and muted lip are still featured, but the real standout is her glossy red nails.
June 1997: The English National Ballet
Dare we say, Princess Diana invented micro bangs and soap nails. In this ethereal look from the English National Ballet in 1997, just months before her tragic passing, the Princess of Wales is seen sporting a short, sleek bixie with ultra-cropped bangs, her classic, natural glam and a subtle-yet-shiny manicure.
