How Princess Diana's Fashion Has Stood the Test of Time

Princess Diana's fashion legacy continues to reign supreme more than two decades after her tragic death.

There's no doubt the late Lady Spencer, whose life was cut short in August 1997 at the age of 36, has left an indelible mark on pop culture with shows and films like The Crown, Spencer and The Princess diving deep into how she redefined the role of a princess, rebelled against the establishment and cemented herself as a style icon in the process.

"She had really sort of transcended fashion and achieved an incredible chic and elegance," Eleri Lynn, Diana: Her Fashion Story exhibit curator, told Vanity Fair in 2017. "All you saw was her, and the clothes became secondary to her own presence and her work."

Even so, Diana's outfits are famous in their own right—on par with Marilyn Monroe's Seven Year Itch white halter dress, Audrey Hepburn's black evening gown in Breakfast at Tiffany's and Jacqueline Kennedy's pillbox hats and bug-eyed sunglasses.

Just a few of her legendary looks include the infamous revenge dress, her biker shorts and oversized sweater combo, her pie-crust blouses and her black sheep sweater.

Even her accessories are memorable, as she called her clutches "cleavage bags," strategically holding them up to her chest when she'd step out of a car. Plus, she also had a knack for chokers and wearing necklaces backward.

But before you can hold the title of a trendsetter, you're just someone figuring out your signature look. The late royal earned the nickname "Shy Di" for her earlier more demure ensembles.

"What's amazing to me," Eleri told Vanity Fair, "when you first meet Lady Diana Spencer, you meet her in her debutante dress from 1979, and it's very frilly, very lacy and very far removed from the fashion icon that she would become."

And yet it's clear that the more Diana evolved so did her approach to fashion.

"You really see the frills and the ruffles of her early romantic style disappearing quite quickly," the museum curator pointed out. "Around the '80s you see the silhouette sleek down."

In fact, it was in 1980 that Diana used her clothes to seemingly communicate to the public. While attending a polo match, she wore a firetruck red knit sweater with a bold pattern that featured white sheep and one black sheep. Many believed the not-so-subtle print was Diana's way of signaling that she felt like an outsider.

But whether or not that was her intended message, the Warm & Wonderful sweater became an instant hit. The label recently collaborated with Sperry to add the print to shoes, further proving the princess's lasting impact.

And who could forget Diana's royal wedding in 1981, where she made jaws drop with her 25-foot, hand-embroidered train with sequins and pearl embellishments.

"She couldn't do a quiet-looking, low-key little gown," designer David Emanuel reflected to E! News in 2021. "The pomp and ceremony and the whole thing, I remember giggling with her."

Another fabulous '80s moment? A polka dot blouse with dramatically puffed sleeves and a peek-a-boo neckline. Worn to a polo match, it was recreated by the late Virgil Abloh in 2017, among other famous Diana looks, for Off-White's spring/summer 2018 collection.

"She was a strong individual," the designer told British Vogue at the time. "Her personal taste was very out of the way from what she was supposed to wear. It's an inspiration."

While many of Princess Diana's looks might seem commonplace these days, more than a few of her choices actually broke royal tradition.

"She was the first member of the royal family to be photographed wearing trousers to evening events," Eleri pointed out. "But she often teamed that with tuxedo jackets and bowties—that's quite the bold, fun look that you don't necessarily expect of a princess."

Even when Diana decided to throw on a black outfit, it redefined what was acceptable for royals to wear. Before then, the shade had only been reserved for a period of mourning.

Of course, her most iconic black look was the revenge dress. The infamous design was not only considered risqué for the time with its curve-hugging structure, plunging off-the-shoulder neckline and short hemline, but it was also a major F.U. to King Charles III (then a prince and her estranged husband).

After all, she wore the daring Christina Stambolian creation to a Vanity Fair fundraiser the same day Charles had his tell-all interview detailing his affair and their broken marriage.

And that wasn't her only fashion clap back either, as she often left the gym in oversized sweaters and biker shorts to deter paparazzi from making a profit off of her photos. In her mind, if she paraded around in the same outfit, then the snapshots would lose their value.

But despite her scheme, the off-duty look continues to be a fave among celebs and influencers alike. Hailey Bieber even recreated the athleisurewear for Vogue Paris in 2019, sharing on Instagram, "All credit and inspo to the amazingly beautiful and iconically stylish Princess Diana."

Regardless of the statement, Diana always dressed with intention. For the public events that involved children, Eleri noted that Diana's clothes were colorful so she'd appear approachable.

"She didn't wear gloves because she liked to hold people's hands," Eleri explained. "She would sometimes wear chunky jewelry so that children could play with it, and she never wore hats to children's hospitals after a while, because she said you couldn't cuddle a child in a hat."

The museum expert added, "If she was visiting hospitals for the blind, she would often wear velvet so that she would feel warm and tactile."

Princess Diana's style may have paved the way for the likes of Kate Middleton and Meghan Markle, but there's no denying that her influence far exceeds royalty. Rihanna, Hailey and Emily Ratajkowski have all cited the People's Princess as their fashion muse.

"I was really inspired by the fact that she was the most-looked-at woman in the world at that time, of all time, and she did what she wanted with her style," Hailey told Harper's Bazaar in September 2022. "She really expressed herself through her style despite being in the position she was in."

(This article was originally published on November 16, 2022 at 10:19 a.m. PT)