Throughout her short but extraordinary life, Diana, Princess of Wales, deployed fashion as a weapon. Born into a culture that belittled women and married into an institution that celebrated suppression, there
were numerous occasions in the princess’s troubled history when the clothes she wore were her most reliable tools of expression. This is a point British fashion writer Eloise Moran makes repeatedly in her upcoming book, The Lady Di Look Book: What Diana Was Trying To Tell Us Through Her Clothes. “She was telling us a story or communicating with us from really early on,” Moran says. “Most people think, ‘Oh, she was only being rebellious in the ’90s.’ There’s actually signs of her rebelling much earlier on.”
Diana's style has since been replicated endlessly, but it's now enjoying a particularly poignant resurgence, both due to the fashion industry’s recycling of ’90s and early-aughts trends, but also thanks to the immense popularity of Diana-centric media, namely Hollywood projects such as The Crown and Spencer. (Her beloved bike shorts-and-sweatshirt look has even inspired its own TikTok trend.) Her little black dresses, broad-shouldered power blazers, and delicate pearls have as much cultural currency now as they did at the height of her popularity, but they've taken on new meaning in the years since her tragic death.
Numerous brands have begun selling dupes, near-dupes, or exact replicas of outfits made famous by the princess. Perhaps the most well-known example is Rowing Blazers manufacturing a number of sweaters worn by Diana in her early years. Other retailers have stocked up on some of the princess’s favorites, including minidresses, pussy-bow blouses, high-waisted denim, chunky sneakers, tailored coats, plaid skirts, and puff-sleeve tops. But Moran says the reason why new generations are falling in love with the princess’s style has less to do with the clothes themselves than with the personality wearing them.
When Moran first created the Instagram account @ladydirevengelooks, she was 25 years old and going through the breakdown of her marriage. She created the account as a way to channel Diana’s own penchant for revenge-dressing in the wake of her divorce from Prince Charles. But as Moran buried deeper and deeper into research, she found more to love about the princess than her off-the-shoulder gowns, and so did her audience: @ladydirevengelooks now boasts more than 118,000 followers.
“The fascination that exists around Diana [today], I don't think it's just the clothes,” Moran says. “Diana really was this kind of feminist figure. She was...this woman who went through this really hard time. She's multi-layered; she won at the end. So I think people really connect with that, especially since we're bombarded with these one-dimensional characters over the Internet. It's influencer world: big butts, Instagram outfits. It's so fake.”
For those seeking to channel Diana's authenticity, Moran provides a few tips: Don't simply regurgitate exactly what the princess wore in her prime. Decide which characteristics of her style feel most reminiscent of your own. Was it her Sloane Ranger phase? Her kitschy patterns? Her voluptuous necklines? Her athleisure? Ask yourself, as Diana did, what message you seek to send with your clothes. Then pick a few investment pieces to build your own look around. For inspiration, we’ve assembled some of Diana's most iconic garments—many of which have been replicated onscreen in The Crown and Spencer—and matched them with similar options you can shop today.
Unquestionably one of Diana's best workwear looks, this ensemble pairs an olive blazer over a white shirt and pants, finished off with a pair of chic beige loafers and a dark brown belt. This would look just as chic on the streets of London today as it did when the princess wore it in 1994.
“In the ’90s, she was hitting 30, and I think once you're in your 30s, you're like wheeling and dealing,” Moran says. “You know your sense of style. And then obviously there's this sharper edge to her where she's like getting back on the men who kept her down in her life.”
Princess Diana loved classic denim; she'd jump at any chance to wear it when she wasn't attending parties or galas. One of her best jean-clad looks is the jumpsuit she wore on a ski holiday with her sons, Princes William and Harry. Paired with a black moto jacket, a brown waist-cinching belt, and chunky white boots, the effect seems trendier today than ever.
First spotted on the princess at her home in Highgrove, this all-pink look was re-created by Emma Corrin in season 4 of The Crown, worn as Diana is getting acquainted with her new surroundings at Buckingham Palace.
It's hard to overstate Diana’s impact on the workwear-meets-casual trend, as seen in this fan-favorite blazer-over-sweatshirt look she sported on the polo field. Rowing Blazers has even re-created a version of the British Lung Foundation crew-neck the princess wore that day—complete with the iconic red balloon.
Another outfit remixed for The Crown, the yellow overalls and floral blouse depicted here perfectly encapsulated Diana's style choices at the time: She was fond of anything soft and feminine, from her bib collars to her wool sweaters.
“She really adopted this fairytale princess look on the polo field, these very country-core sweet pastels,” Moran says.
Once Diana had grown more understanding of her role as Princess of Wales, she started shifting her fashion choices. In the ’80s, Moran says, she filled her closet with patterned coats, blazers, and skirts—whether plaid, tartan, checked, or houndstooth, she adored them all. This black-and-white houndstooth blazer, paired with a bold black hat, was an instant classic.
Kristen Stewart wore a version of this holiday-inspired tartan blazer-dress while filming Spencer, which is set over a particularly contentious Christmas at the royal estate of Sandringham.
“It's interesting to look at her collar progress through the years,” Moran says. ”If you look at the way her style progresses, it goes from being the super buttoned-up pie-crust collar, to oversized princess collars, to pussy-bow blouses. And then she ditches the big collars completely for men's collars.”
Another Lady Di look beloved for its symbolism is her black-sheep sweater, one of several cheeky—and perhaps gauche—sweaters she wore during her early years in the royal circle. Despite the bold pattern (or maybe because of it), the look is cherished as one of Diana’s most meaningful fashion choices as she struggled to stand out within the The Firm.
The puff-sleeve has made a major comeback in the years since Diana’s death, and this black-and-white blouse is almost a sure bet to appear on season 5 of The Crown, in which Elizabeth Debicki will take over for Corrin.
This wouldn't be a story about Diana's fashion if we failed to discuss her famed athleisure looks, in which the princess paired sweatshirts over bike shorts while running around London. One of Moran's most prized possessions is a sweatshirt identical to the one Princess Diana was photographed wearing as she left the Chelsea Harbour Club in November 1995.
“I have some original Ralph Lauren USA sweatshirts, two of the exact same ones she had,” Moran says. “And then I also have an original Virgin Atlantic sweatshirt, which is really rare. I love a long sock with it—an ankle-length sock with a sneaker.”
Attempting to re-create Diana's gowns on a budget is an understandable undertaking—it's unlikely you have the pocket change the royal family happened to have on hand—but there are still ways to assemble looks reminiscent of her red-carpet stunners. The princess wore this gorgeous dress by designer Catherine Walker while attending a performance of Swan Lake. By pairing a cinched-waist long-sleeve white blouse and pale-pink skirt, you can easily emulate the real thing.
Some of Lady Di's most eye-catching garments were outerwear, as is the case with this yellow checked coat, but you can create a similar effect with a crop top and maxi skirt. This set from Anthropologie uses a similar design, and by adding in mid-calf boots and a thick waist belt, you can further match the princess. Or you can mix up the look by incorporating other Diana favorites: “If you want key pieces [of Diana’s],” Moran suggests, “I think a pair of chunky sneakers, a really sharp tailored coat, a blouse with a puff sleeve, and a [top with an] interesting collar detail.”
Perhaps Princess Diana's single most iconic outfit, this Versace off-the-shoulder dress—widely labeled the “revenge dress”—was seen as a not-so-subtle middle finger to Prince Charles in the wake of the couple’s separation. Debicki was recently spotted on the set of The Crown wearing the dress, a development that threw fans into an uproar.
Ever an essential, the simple white button-down was a wardrobe staple throughout Diana’s life, but perhaps its most famous appearance was during her three-day trip to Bosnia in 1997, during which she led a powerful campaign against landmine use.
The People's Princess was never one to shy away from color, and this red-and-pink blazer-dress remains one of her most vibrant get-ups. Corrin wore a similar version during season 4 of The Crown, further solidifying the legacy of the two-tone ensemble.
This story will be updated.