Princess Diana’s 30 Most Iconic Style Moments of All Time, From Her Wedding Gown to Revenge Dress

The Gist

• Princess Diana is known for so many remarkable achievements—from being an incredibly devoted mother, an inspiring public figure and role model, to a fashion icon.

• From her ginormous wedding gown to her newsworthy ‘revenge’ dress, Princess Diana’s style has become simply iconic.

Princess Diana is known for so many remarkable achievements—from being an incredibly devoted mother to an inspiring public figure and role model. Regardless of whether she was tending to her children or shaking hands with Mother Teresa, she did so with style and grace. After all, Lady Di had an unforgettable fashion sense. Her standout sartorial moments, both within the royal family and beyond, have even earned her the title of fashion icon with outfit formulas that are still in season. And it wasn’t just her royal wardrobe that garnered attention either.

As a royal, Diana’s style leaned conservative—marked by structured suits, covered-up gowns, and classic, modest dresses. But after her 1996 divorce from then-Prince Charles, she broke free from the constraints of royal dressing, embracing more daring, bold looks that showed off her personality. Regardless of what she wore, it was always uniquely Diana, inspiring others to dress confidently and according to their own rules.

Keep reading to revisit 30 of Princess Diana’s most iconic style moments.

Preppy Princess-to-Be

One of the reasons that the public fell in love with Diana in the first place was that she was never scared to show how she was feeling. In this purple-on-purple preppy look, Lady Di seems sweet—if not a little bored.

Peeking Through

Still lacking a royal clothing allowance, the teenaged teacher’s assistant topped her romantic pink evening gown with a plain wool coat for Princess Margaret’s 50th birthday bash.

The Princess Bride

She collaborated on her wedding gown with little-known design team David and Elizabeth Emanuel. “In the end, the design process was quite simple because it was just the three of us,” the duo wrote in A Dress for Diana. They had the future princess slip sample dresses on over her jeans: “She was terribly excited to be trying on huge bouffant petticoats, satin skirts, and boned bodices.” The final garment was made of British-woven silk and featured a dramatic 25-foot train.

Hunt and Gather

When Shy Di met with the press on her Scottish honeymoon, her finery was limited to her Welsh gold wedding ring inscribed with a message from the prince: “I Love You, Diana.”

Something Blue

The expectant princess made headlines in a single-shoulder, drop-waist Bruce Oldfield gown in vivid, blue silk. “The English rose syndrome was never my bag,” the designer once told a biographer. “I liked to see her in much simpler things.”

Metallic Muse

The princess was nicknamed “Dynasty Di” by the tabloids because of her wide-shouldered gowns, like this silver Bruce Oldfield. “She was very involved,” Oldfield has said of his client’s wardrobe, but “you’d have to be fast because she didn’t have much patience.”

Red(ish) Velvet

Diana wore this wine, velvet Catherine Walker dress to a London premiere in 1985. Although it looked conservative from the front, the gown had an open back that the princess accentuated with a long pearl necklace worn backward.

Suit and Tie

The Princess of Wales knew how to wear a dress like no one’s business, but she could also pull off business attire. This green Jasper Conran number, complete with a matching tie, is a great example of her gender-bending ‘fits.

Bolero Babe

Designer Victor Edelstein has said that the dresses he made for the princess were a collaboration: “You each make suggestions and ask, ‘What do you think?'” In the case of this white gown and bolero, the partnership paid off. Years after she wore it to a New York event, she chose a photo of herself in the ensemble for the cover of her Christie’s auction catalog.

Unconventional Tiara

For an appearance in Melbourne, Australia, Diana accented a single-shoulder gown with an emerald-and-diamond choker worn as a tiara. The necklace was a wedding gift from the queen, who likely imagined the deco treasure being worn in a more conventional way.

Gingham Girlie

In 1986, Shy Di posed outside on the steps at her country home in Highgrove. The hot pink sweater layered over a white long-sleeve blouse gives preppy, especially when paired with gingham pants.

Dark Navy Velvet

Victor Edelstein based this dark navy, velvet column gown on Edwardian evening designs. The princess famously wore it for a spin on the White House dance floor with John Travolta.

Equestrian Off-Duty

Proving that she needed little more than her statuesque frame to make an impression, Diana strolled the grounds at the Guards Polo Club in jeans and a sweatshirt, topped with a crisp blazer.

Ultimate Brit

Diana attended a U.K. wedding in a white sheath dress and dove-gray coat accessorized with a traditional British wedding hat—and an even more traditional British umbrella.

Princess in Pink

The princess coupled her beaded ball gown from Catherine Walker with the Spencer tiara. She was known to have dresses altered for future wearings; a version of this gown with a narrow skirt would later sell at auction for $51,750.

Mother of Pearl

The high collar on this Catherine Walker pearl-encrusted bolero was inspired by Elizabethan ruffs. The less historically minded press christened the ensemble “the Elvis dress.”

Porcelain Florals

For the Canadian premiere of Crocodile Dundee II, Princess Di chose a floral-print, ruched dress by Catherine Walker. The extra fabric cascading down the princess’s side adds tons of interest and dimension to the look.

Lady (Diana) in Red

Princess Diana looked radiant at a London Kire Te Kanawa concert in a raspberry-hued Victor Edelstein gown. She gave Chris de Burgh’s 1986 “Lady in Red” a whole new meaning.

Green Moment

The princess visited the British School of Seoul in South Korea wearing a fitted green suit with matching pumps. It was equal parts academic, professional, and royal.

Barbiecore

A hot-pink frock coat and matching skirt gave the newly separated Diana a cheerful glow. Pink hues always helped bring out Lady Di’s more playful side, which you can see here via her beaming smile.

The Revenge Dress

It was the LBD worth a thousand words: In 1994, just as a documentary regarding her husband’s infidelities was airing, Princess Diana strolled into a Serpentine Gallery benefit wearing this iconic number from Greek designer Christina Stambolian. The next day, every front page was devoted not to the Prince of Wales’s televised confession but to images of the glowing, confident 32-year-old Diana.

Ever mindful of the power of fashion, three years later, she auctioned off 79 of her favorite gowns at a Christie’s auction that raised $6 million for AIDS and breast cancer charities.

Seeing Red

As a royal, Diana was required to wear British designers to boost the local economy. Post-separation (which was in 1992; the divorce was made official in 1996), Diana often donned international couture like this crimson Christian Lacroix dress, worn in Paris in 1995.

Not-So-Shy Di

What happened to Shy Di? The princess began to favor sheath dresses that showed off her slim shape, like this white Versace number she wore to a charity concert in Italy in 1995. Seems like the black gown wasn’t her only revenge dress.

Bead Me Up

Diana showed off her toned shoulders in a plunging, beaded cocktail dress by Catherine Walker. The beads help give this already-polished look a little playfulness and sparkle.

Jackie O-Inspired

Gianni Versace designed the Princess of Wales’s Jackie O-inspired pink suit for a visit to the nation’s troops. Her pillbox hat was by Philip Somerville. It was all proving that she could stand on her own.

Athleisure

It’s hard to go out these days and not run into someone donned in athleisure. The trend, which mixes athletic wear with comfortable loungewear, was Princess Diana-approved. In fact, she wore a crewneck and biker shorts out in public several times.

Nod to Culture

The Princess wore an ivory, pearl-studded shalwar kameez to a cancer fundraiser in London in 1996. The pantsuit, which was a gift from her friend Jemima Khan, inspired her to commission similar Pakistani-inspired outfits from Catherine Walker.

Public Service

Diana visited patients at an Angola hospital wearing a sleeveless chambray shirt and trim chinos. Even as a casual look, it still serves.

Saintly White

Diana met with Mother Theresa in New York in a simple white suit and cap-toed pumps. This serves as another example of pared-down clothes still being fashionable enough to be in the public eye.

Simple Yet Stunning

While Princess Di’s royal looks were classic, her post-divorce looks helped people see more of her—in more ways than one. Her figure-hugging Catherine Walker dress and Jimmy Choo shoes accented her long legs.

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