The late Princess Diana had a fascinating style evolution. She started her public life as a young woman thrust into sudden media attention when she began a relationship with then-Prince Charles. With the benefit of style teams, a royal budget, and the experience of going to hundreds of public events, she became a style icon. Her outfits were praised—sometimes scrutinized—and she learned the perfect balance between chic and event-appropriate. But something interesting happened as she separated and divorced from Charles: Her clothes became somewhat more daring (including, in its most extreme example, her “revenge dress” that made her look stunning in the face of Charles’ infidelity) and, while still appropriate for whatever gala she was attending, more expressive of her style. She also incorporated more suits and tailored dresses into her wardrobe, and unveiled a sharp, shorter new haircut. She managed to attain a measure of joyful dressing before her death by wearing clothes that seemed to make her feel most like herself—away from her marriage and former royal requirements.
Ahead, 32 of Princess Diana’s most iconic style moments, which mark just a few important moment on her long trajectory towards fashion independence.
At Buckingham Palace, 1981
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The story of Diana’s engagement outfit is apparently straight out of a movie: Originally she stopped at high-end store Bellville Sassoon, where she was not recognized and was encouraged to shop elsewhere (ouch). Then she went to Harrods and got something off the rack—this blue Cojana skirt suit—which worked perfectly with her blue engagement ring. Proof that Diana’s style had major impacts in every facet of society: Kate Middleton would also wear a blue dress when she got engaged to Prince William with the same sapphire ring.
At Wetherby Taking Her Sons to School, 1989
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Proving just how good Diana was at style, including casual, “just dropping the kids off at school” style, this outfit wouldn’t make sense on paper: billowy white pants and sweatshirt, cowboy leopard print boots, a pinstripe blazer, and a baseball cap? Us mere mortals could never pull it off. But by following a few simple style rules—having the base outfit be a neutral white and all the accessories working as complementary parts—Diana made it look easy.
Leaving Chelsea Harbour Club, 1995
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Just call her the pioneer of athleisure! Never had a pair of bike shorts stirred more excitement, as Diana (leaving a workout) paired them with a graphic (Virgin Atlantic) sweatshirt, socks, and sneakers. Post-separation, Diana had more casual, off-the-cuff fashion moments like these, where she was seen running errands or getting out and about during the day. Her reclaimed independence was something we absolutely saw through her clothes.
At Windsor Polo Event, 1980
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With some weird foreshadowing at play, this ‘Black Sheep’ wool jumper by Warm and Wonderful would be an interesting clue about how Princess Diana felt about being married to Charles and royal life in general. The brand continued to sell the sweater long after Diana initially wore the jumper, and in 2023 Sotheby’s sold the original for $1,143,000(!), according to ABC. It was a world record for any jumper (i.e., sweater) ever sold and a record for one of Diana’s clothes.
At the Braemar Highland Games in Scotland, 1981
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Diana paired this tartan dress designed by Caroline Charles with a black Tam o’ shanter style hat (a traditional Scottish bonnet), which makes sense for this event in Scotland. This was a royal rewear, with Diana rewearing the suit but changing up the neckline. Diana loved a royal rewear as much as other royals, but she was innovative in how she edited and tailored her clothes so that even though it was the same piece of clothing, it looked totally different with the modifications.
At Guards Polo Club, 1988
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Of all the emulatable styles that Diana pioneered, it was probably her casual style (often when she wasn’t dressing for an event or when she knew she’d be photographed) that people loved the most. One of her most iconic images is this photo, with blue Levi jeans tucked into cowboy boots, with a British Lung Foundation jumper and baseball cap to top off the look. The perfect mix of casual, layered, and a bit masculine means this outfit has been and continues to be referenced in street style.
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Here, post-separation, Diana is just casually shopping in white cigarette pants, cream turtleneck, and long hunter green blazer, with two-toned loafers and a two-toned tote and matching brown belt. It’s very minimal ’90s, which makes it all the more fun since royals often opt for classic silhouettes that don’t dip into trends. It’s another outfit that’s easy to recreate—and one that people cite as an example of why Diana’s style captivated people so much.
At Highgrove House, 1986
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In Diana’s most casual moments (just out of frame is a toddler Prince Harry playing), it felt like she channeled her most authentic style. Pink was a favored color of Diana’s and she wore the hue in a lot of different shades, but this gingham pant and matching sweater feels like the perfect balance of feminine and tailored. Feeling literally at home, she didn’t put on as many frills and ruffles: just simple, elevated, but still pretty basics.
Arriving to Hong Kong, 1989
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Diana loved combining red and purple (see also her suit at the Taj Mahal and her one-shoulder dress in Thailand). As one of the national colors of China is red, this was also a thematic choice for Diana to use at her arrival. Here, she’s pulling off that tricky combination: wide brim hat, purple skirt with matching pumps, and a red jacket. Visible to onlookers from hundreds of feet away, it was a perfect arrival look for the princess.
In the Hong Kong Culture Centre, 1989
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The so-called Catherine Walker “Elvis dress,” which she wore again to the 1989 British Fashion Awards, is one of Diana’s more divisive looks. The pearl detailing was a nod to Chinese culture, but the over-the-top white collar felt too ’80s even at the time for some critics. Biographer Tina Brown recounted an anecdote where Prince William even commented, “Mummy, that’s too awful to sell” when she added it to a pile of gowns for an upcoming Christie’s auction. And yet: It’s distinctly associated with Diana.
At the Taj Mahal, 1992
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While Diana drew headlines for different reasons at the time (sitting at the Taj Mahal, renowned symbol of love, alone and looking miserable) her outfit was a pretty colorblocking choice: red blazer, cream top, purple skirt and matching pumps. Meghan Markle would later go on to choose a red and purple colorblock look while she was pregnant that reminded royal style experts of this exact moment—we love a royal tribute.
Aboard the P&O cruise liner “Royal Princess,” 1984
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What does one wear to an event where a ship is being named after you? Wearing a charm bracelet, of course! This red skirt suit and matching beret with black trim and matching black accessories is considered pretty quintessentially Princess Diana fashion: conservative and appropriate for a formal royal event, but with some flair, individuality, and fun. This photo, of her looking up at the “Royal Princess,” is one of her most well-known images.
Leaving St. Mary’s Hospital With Prince Harry, 1984
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Diana wore a Jan van Velden red coat as she left the hospital to debut Prince Harry: It has some structure with an oversized feel, which…is the exact outfit I would wear if I had to leave the hospital with a baby and immediately be captured by photographers. An underrated aspect of Diana’s style was her iconic choice of coats and coat dresses, something that would be emulated in royal women to follow (including Kate Middleton and Meghan Markle).
At a Banquet in Auckland, NZ, 1983
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Much like the tiara (which looks to be the Lover’s Knot), this Gina Fratini dress is a lot of look. It’s part of the princess’ early style—and actually hearkens back to her wedding dress from two years earlier. This was part of the Royal Tour of Canada, so it makes sense that Diana would dress in a floor-length gown, and it’s a testament to her style chops that she’s making this very big dress work for her. She’s wearing it, not the other way round, in other words.
At the Royal Opera House, 1982
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It’s unclear who designed this dress, but Diana—still early in her marriage to Charles—wore this pretty red and gold sparkly gown at one of her first post-wedding royal events (it was a royal rewear, having debuted the dress at the premiere of the Bond film For Your Eyes Only). While it was still a more youthful cut than some of her later styles, it was a nice foreshadowing of the more daring outfits she would later debut.
At a Gala Evening In Aid Of Cancer Research At Bridgewater House, 1995
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Diana didn’t always turn to black as one of her favorite colors, but when she did, she absolutely made a statement and turned every head in the building (see also her revenge dress, which she had worn just a year prior in 1994). This Jacques Azagury floor-length ballgown wasn’t quite the same kind of statement—it was just incredibly chic, paired with one of her favorite pearl and sapphire necklaces (the center stone adapted from a broach).
At the Covent Garden Royal Opera House, 1989
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This Catherine Walker (another rewear, originally debuted in Melbourne during the Royal Tour of Australia) was a stylish choice for the princess, and one of the delineated moments where she chose a brighter, chic, more streamlined outfit. It was the absolute perfect choice: The play she was watching was Romeo and Juliet and the patterned dress absolutely (intentionally or unintentionally) corresponded with some of the plays most romantic lines: “A rose by any other name,” anyone?
At the America’s Cup Ball, 1986
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This flamenco ball gown designed by Murray Arbeid (who also designed at least one other cool, architectural gown for Diana) is truly one of the more fun and daring dresses that Diana ever wore as a royal. The contrasting opera gloves, the matching black choker—it may have been for the America’s Cup Ball, but that doesn’t mean formal had to be boring. It was also a hint at the fun and sometimes quirky style that Diana was capable of.
At Heads of State VE Remembrance Service in Hyde Park, 1995
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Some of Diana’s most iconic moment were with her sons, like here in this blue skirt suit, stacked pearl necklace, and pillbox hat as part of Remembrance Service (by then, on the way out of her marriage but still attending some events). Light blue was one of her favored colors, and Kate Middleton has continued on the tradition with a host of light blue outfits as well. She’s also broken out a matching pillbox hat for more formal occasions.
At the Cannes Film Festival, 1987
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This pale blue Catherine Walker and matching scarf around the neck was a fun and bold choice for Diana—not the color, which was a pretty and conservative blue, but the strapless construction (and it would be a style she would return to again and again). The inspiration was Grace Kelly’s character in Alfred Hitchcock’s To Catch A Thief (an icon borrowing from an icon, so to speak), and it remains one of Diana’s most remembered gowns—and a royal rewear, so Diana must have liked it.
At the Christies Show, New York, 1997
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This white and light pink floral Catherine Walker dress is a classic (paired with another royal-favored designer, Jimmy Choo shoes) but more daring than a typical royal dress might have normally been. Diana had worn a similar style of dress in 1995 (that one a white Versace), and it felt like a natural progression of her post-royal style. Even something this “daring” was a nice change and a liberating sartorial choice for Diana.
At the Gala Dinner At Field Museum Of Natural History, 1996
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This Versace dress and matching Jimmy Choo pumps were part of Diana’s colorful red carpet life (and seemed to coincide with a happier time in her life, where she debuted more avant-garde, fun pieces, even to the most formal events). Royals often used to stick to British designers, so according to royal experts, in her “post-royal” life, she branched out to other designers that she may not have felt comfortable wearing prior to this.
At the Victor Chang Research Institute Dinner Dance, 1996
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This blue Versace gown was an absolute standout of Diana’s later style. It was colorful, it was daring, it was a designer she favored in her later style without as many royal restrictions. Vogue called Diana the “unexpected Versace poster girl of the ’90s,” and this may be the most notable example of it. And, even with this more avant-garde style, Diana still opted for chic and tonal, proving that she was still operating within a smart, high-fashion dress code.
In Bonn, Germany, 1987
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This off-the-shoulder black dress by Victor Edelstein was a favored choice of Diana (she danced with John Travolta at the White House in 1985 in it) is here paired with the Spencer Tiara and earrings that were a gift from the Sultan of Oman. This dress sold in 2019 for $347,000, and is considered one of her more chic outfits of all time.
At the British Embassy, 1988
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This maximalist Catherine Walker red and black one-shoulder gown is one of the instances of Diana’s precise styling as she became a more mature working royal. It was a definitively ’80s style outfit, but the a-line structure and classic one-shoulder construction at the top meant that the look was complex but not busy. It would also be a perfect instance of Diana daring to show a little skin in her outfits, without running too afoul of royal protocol.
At the Elysee Palace, 1988
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This white and gold Victor Edelstein dress (with a conservative long sleeve and ornate patterning) was a favorite of Diana—a royal rewear, worn again at a Wintergarden gala in 1989. A portrait of her in the dress was also used on the cover of magazines when they would pay tribute to her and her passing—the gown made her look incredibly regal, regardless of whether she was wearing a tiara with it. It was also a more modern iteration of the white color she loved.
At the Vienna Burgh Theatre, 1986
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Diana commissioned Catherine Walker for this stunning blue dress. And, no surprise, it ended up being a royal rewear, with Diana wearing it again in 1990 at the Diamond Ball (in that iteration, she wore it with a matching blue choker and blue pumps, giving us a full tonal outfit). Even with the very ’80s shoulder pads and front slit design, it’s aged incredibly well, particularly its floor length design and shimmery color. When it went up for auction, it sold for £96,000.
At the National Gallery in Washington, D.C., 1985
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This Hachi dress was another dress that Diana liked to rewear, particularly for events that mandated the most formal of dress codes. White was a color that Diana went back to often—perhaps not as over the top as with her wedding dress, but often in chic, column styles. This was one of her fan-favorite looks, and a dress that has aged exceptionally well. Clearly we’re not the only ones who agree: When it went up for auction, it sold for over $75,000.
At a Banquet at Claridges, 1989
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To attend an event hosted by the ruler of the United Arab Emirates, Diana brought out the Spencer Tiara (apparently more comfortable than the Lover’s Knot, which makes sense because it’s more delicate) and this Bruce Oldfield red gown. Even though a deeply ’80s silhouette like this sometimes feels dated, with a fitted bodice past the hips and then a flare at the bottom, this particular dress is subtle enough to feel classic and chic—something that any royal could wear now and look just as put-together.
At the ‘A View to a Kill’ Premiere, 1985
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This gold lamé Bruce Oldfield dress is the perfect choice to the premiere of a Bond film—the royals often break out their very best gowns for these events, and this was no exception (it’s a royal rewear, debuted in 1980). Kate Middleton was thought to have been inspired by this dress when she debuted a (similarly glittery) gold Jenny Packham to the premiere of No Time to Die, in 2021. Of all the gowns from Diana’s impressive collection, this has to be one of the most eye-catching.
At a Vanity Fair party at the Serpentine Gallery, 1994
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It’s hard to overestimate the impact of this dress on the public. Princess Diana and Prince Charles were engaged in a contentious separation, and Prince Charles had just confessed on national TV that he had been unfaithful, but only after the relationship had broken down (ouch). Princess Diana had originally deemed this Christina Stambolian dress to be too provocative to wear, but after the original outfit she’d planned to wear to the Serpentine Gallery fell through, it turns out this was exactly the right choice for the normally more buttoned-up royal. It became the stuff of legend.
At Her Wedding to Prince Charles, 1981
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Arguably the most famous wedding dress ever, the detail people most remember from that day is the 25-foot train that trailed ever-so-glamorously from Diana’s billowy dress. The dress was made of silk and taffeta, mother-of-pearl sequins, and an estimated 10,000 pearls sewn by hand. According to designer Elizabeth Emanuel speaking to People, “We never had any special instructions about how to make the wedding dress. That added a bit to the fun of it all, made it bit of an adventure.” The resulting (very ’80s) gown absolutely became the gold standard of wedding gowns for the next decade.
