Princess Diana’s Most Iconic Beauty Moments Are More Applicable Than Ever

Forever fabulous.

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No matter how many years pass, Princess Diana’s legendary combination of kindness, compassion, and chic aesthetic choices continue to endear her to new generations. Here, look back at some of. the late royal’s iconic beauty moments — they’re the ultimate haircut and makeup inspiration.

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At just 20 years old, young Diana Spencer favored soft, girlish hairstyles and very minimal makeup that showed off her fresh-faced beauty. In 1981, just before her marriage to Charles III, her polished take on the shag is a sweet ‘70s holdover.Central Press/Hulton Royals Collection/Getty Images
Leaning into the classic “English Rose” style of makeup combined with the decade’s trademark boldness, Princess Diana would often concentrate bright pink blush at her temples, as she did in Australia in 1983 — a trip famously recreated in The Crown Season 4.Tim Graham/Tim Graham Photo Library/Getty Images
With her longest-ever hair as an adult, Princess Diana tried out all sorts of versatile hairstyles and accessories on the shoulder-skimming bob. These classic hair combs’ tortoiseshell pattern are a perfect pairing with her preppy wool overcoat in 1984.David Levenson/Getty Images Entertainment/Getty Images
Long before “I’m Cold” makeup took TikTok by storm, a 1985-era Diana got the same effect with rosy blush made pinker by the cold while skiing, her voluminous feathered hair fluffed up around her red coat.Georges De Keerle/Hulton Archive/Getty Images
Ever an aesthetic risk-taker, Princess Diana converted this emerald-inlaid choker into a bold headband on a trip to Australia in 1985. In a sweet tribute, future daughter-in-law Kate Middleton would wear it on a trip to Boston in 2022 — as a necklace, though.Anwar Hussein/WireImage/Getty Images
Princess Diana’s blue eyeliner and mascara might be her most memorable beauty look ever, a trend that’s seen a serious resurgence in recent months. The original look was created for Di by makeup artist Mary Greenwell. Fun fact: Greenwell would later mentor and train Charlotte Tilbury.Mirrorpix/Mirrorpix/Getty Images
In 1990, hairstylist Sam McKnight gave Diana the close-cropped, semi-feathered haircut that would define ‘90s style as a whole. In his book, McKnight recalls spontaneously suggesting the cut after her famous Demarchelier photoshoot, and she gamely agreed on the spot.Princess Diana Archive/Hulton Royals Collection/Getty Images
It was also McKnight who suggested a slicked-back look for Princess Diana’s appearance at the 1995 CFDA Awards. He details remembering how chic she looked with her hair combed back after the shower in his memoir, and suggested they try it with gel for the ceremony.Tim Graham/Corbis Historical/Getty Images
By 1997, Princess Diana’s hair had grown out a bit, and she often wore it blown straight for sleekness and volume. Paired with lash-skimming bangs for a long pixie effect, the haircut commanded attention at a party.Tim Graham/Tim Graham Photo Library/Getty Images
Princess Diana only ever made one appearance to the annual Met Ball, but her attendance in 1996 — decked out in a lace-trimmed slip dress with berry-toned lipstick and oh-so-’90s square French tips — is still considered an all-time best gala moment.New York Daily News/New York Daily News/Getty Images

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