8 Celebrities Who've Channeled Princess Diana’s Style Perfectly

Updated on Nov 12, 2020 at 12:45 PM

The new season of The Crown drops on Netflix on Nov. 15, and all eyes will be on Princess Diana‚ played by newcomer Emma Corrin — who makes her entrance in the fourth chapter of the hit series. While the episodes are set to recount her tumultuous relationship with Prince Charles, this season will, for many viewers, also be a reminder of her unique and incredible fashion sense.

From the iconic Catherine Walker tuxedo-style suit (she was the first female royal ever to wear trousers to an evening event) to that sexy, off-the-shoulder "revenge dress" she wore the same night Prince Charles confessed to adultery during their marriage in a television interview, the Princess of Wales understood the power of fashion. And she enjoyed making bold choices. Often dressed in black — a color that is usually only worn by the royal family for mourning — showing off her bare shoulders and knees, and wearing art deco emerald chokers as tiaras, Diana broke the royal dress code more than once. "I don't go by a rule book," she famously said; and this was true for her style choices, too.

Princess Diana created some of her most headline-making moments when decked out in evening gowns and crown jewels. But when Lady Di wasn't busy being a princess, it was her street style that had everyone talking. Regularly photographed in straight-leg jeans, an oversize jumper, and a baseball cap — her go-to look for dropping the kids off at school — she sported athleisurewear long before it was a common term in our fashion lexicon. Those paparazzi shots of Princess Diana running errands in London in navy biker shorts and a grey Harvard sweater are iconic and undeniably the inspiration for Hailey Bieber's preferred off-duty look.

And Hailey isn't the only celebrity to draw inspiration from the late royal. Many actors and models — on and off the red carpet — have re-created some of Princess Diana's most memorable looks from the '80s and '90s, so we've gone ahead and listed some of our favorite royal fashion copycats.

Emily Ratajkowski

Donning a stone-colored, shoulder-padded blazer and vintage blue jeans, the model/actor is a spitting image of the royal as she walked her dog in New York. She previously even told US Weekly in an interview that, "I'm trying to go '80s and have been thinking about Princess Diana's street and ready-to-wear moments like a blazer and a bike short and a big sneaker."

Harry Styles

Harry Styles made headlines last year when he stepped out in a blue sheep-printed knitted vest by Lanvin. The internet was quick to point out the similarity between the singer's designer piece and the red woolen sheep jumper Princess Diana wore to a polo match in 1981. The statement knit was recently rereleased and is available via preorder, but if you can't get your hands on it, there's always the original knitting pattern that you can use to make it yourself.

Ella Fanning

Diana stunned twice in this pale blue Catherine Walker gown — once at the Cannes Film Festival in 1987 and one more time for attending a performance of the musical Miss Saigon in London two years later. In 2017, actor Elle Fanning went for similar Cinderella vibes as she dressed up in a strapless design by Miu Miu for the Met Gala.

Gigi Hadid

Recreating one of Lady Di's most casual looks — which she wore for a visit to The Regiment in West Berlin, Germany — the supermodel stepped out for dinner in New York in a matching black-and-yellow Polo Ralph Lauren zip-up jacket and drawstring joggers.

Angelina Jolie

The Maleficent actor attended the 2018 BAFTAs in a black velvet Ralph and Russo design with sweetheart neckline that closely mirrored Princess Diana's "Travolta dress" — the midnight-blue, off-the-shoulder gown by Victor Edelstein she wore to dance with actor John Travolta at a 1985 state banquet at the White House.

Hailey Bieber

One of the biggest fan's of Princess Diana's street style — she even did an entire photo shoot with Vogue Paris to prove so — Hailey Bieber was spotted heading out for brunch in Beverly Hills in in outfit that closely resembles the baseball cap, crew neck, jeans, and cowboy boots combination Diana wore to a polo match.

Marisa Tomei

Embracing the colorblock trend, actor Marisa Tomei walked the red carpet of the 2019 Emmy Awards in a one-shouldered Ralph & Russo design with knotted detail. Back in 1988, Princess Diana wore a nearly identical red and purple chiffon dress — another beautiful evening gown by Catherine Walker — during a state dinner in Bangkok, Thailand.

Kendall Jenner

Proving that cowboy boots and sweatpants go together, Kendall Jenner channelled Diana in one of her most unexpected off-duty looks. Skipping the baseball cap and blazer, the supermodel went for a green sweatshirt, Adidas tracksuit bottoms, and white western boots.