Princess Diana's Best And Worst Looks

Among her roles as a philanthropist and doting mother-of-two, Princess Diana is remembered as one of the greatest style icons of the 20th century. The Princess of Wales redefined the way we look at royal fashion — mainly, we're totally obsessed. Think about it: Would Meghan Markle's ASOS dress, as Marie Claire noted, sell out practically immediately if Diana didn't set the precedent? Would Kate Middleton's Zoom conferences basically read like a quarantine issue of Vogue? We think not.

With the fourth season of The Crown, Netflix's historical drama-slash-reluctant fiction, Princess Diana's most memorable looks have been brought back into the spotlight, and the series actually got it pretty darn close. According to Refinery29, costume designer Amy Roberts and assistant costume designer-slash-head buyer Sidonie Roberts used actual photos of the royal family to guide the construction of the costumes. 

Of course, because Princess Diana was mainly elevated into the spotlight during '80s and early '90s, her most iconic looks are an absolute frenzy of shoulder pads, pastels, billowing ruffles, kitschy sweaters, and statement hats that most of us couldn't dream of pulling off. Basically, her wardrobe is the absolute best that the worst trends of the era have ever looked. 

For better or for worse, these are some of Princess Diana's most memorable ensembles. Whether The Crown will single-handedly thrust shoulder pads back into fashion is still to be seen.

There was a time when Princess Diana was not a princess and merely a teenaged fiancée. As Town & Country noted, Lady Diana Spencer was just 19 years old when Prince Charles proposed after about six months of dating. It was a modern day fairytale not too dissimilar from Prince Harry and Meghan Markle's whirlwind romance, and her wardrobe reflected her lifestyle. It was far more casual prior to officially joining the royal family, but if there's one thing she never lost, it was her penchant for kitschy, statement sweaters.

In this shot from 1980, Princess Diana dons an animal-emblazoned Fair Isle cardigan as she leaves her flat (as hard as it is to believe, she once had flatmates just like everyone else). The ruffled collar of her button-down — complete with a dainty ribbon tied into a bow — was iconic enough to land a spot in The Crown. You can see her character wearing something similar in the scene where she's picking out an engagement ring.

In 1981, Princess Diana wore the gown that changed everything. The black satin Emanuel dress that she donned during her first official public engagement with Prince Charles was a carefully curated look that helped push her image away from that of a nursery school teacher and into her new role as the People's Princess.

According to Vogue, Lady Di enlisted Elizabeth and David Emanuel to craft a series of feminine looks that suited her new life in the royal family. "It was all pale pink and baby blue netting and sequins," Elizabeth told the magazine, revealing that Diana was a "true sweetheart with not a lot of knowledge about fashion." This strapless black gown, however, was not one of those custom looks. Rather, Diana saw it hanging in a showroom during her wedding dress fitting and fell in love. Sometimes, fashion just finds you — you don't find it.

Diana's Emanuel dress subsequently made front-page news. Its inky color was widely regarded as inappropriate and too dour for the event, and the form-fitting cut and shoulder-baring shape was considered scandalous. Today, it's in the history books.

In 1981, Princess Diana channeled a Disney princess with more than just her chiffon, off-the-shoulder Bellville Sassoon gown. On November 4, 1981, the People's Princess was transformed into a real-life Princess Aurora when she famously nodded off during "The Splendours of the Gonzagas Exhibition Gala" at Royal Albert Hall in South Kensington, London. As Vogue writes, she was "a modern-day Sleeping Beauty, a princess from a fairytale, facing the hard, real world of constraints imposed by her rank and intrusive paparazzi." The now-infamous photo of Diana quietly napping in a red velvet chair as she's enveloped by the fabric of her puffy gown made her lilac dress famous and forced Buckingham Palace to announce her pregnancy. As all mothers know, pregnancy is exhausting.

According to Hola!, Diana's first pregnancy was seen as an "unexpected turn of events." The 20-year-old princess had only been married for about four months. It took all of a single day for Buckingham Palace to come clean with the news after her (frankly relatable and slightly embarrassing) incident.

Throughout her royal career, Princess Diana may have very well been the queen of statement coats (if that honor didn't go to the actual queen). Her maternity fashion was no exception, as is evident with the red Bellville Sassoon coat she wore the day she announced to the world that she was pregnant with Prince William. Her royal highness even played off the blue threading by accessorizing with a cobalt John Boyd cap and matching pumps. Basically, primary colors have never looked so good outside of a box of Crayola crayons.

Years after-the-fact, Harper's Bazaar dubbed Lady Di's outfit one of the princess' best maternity outfits, but we'd argue it's one of the best of any looks. She oozed confidence, and you'd never know the immense pressure that she was under at the time. In Diana: Her True Story (via People), the princess revealed that dealing with the press was "unbearable" during her first pregnancy and part of the reason why "William had to be induced." She couldn't tolerate the pressure generated by the press any longer, and not much has changed for the royal family over the years; Meghan Markle echoed the same cries throughout her own pregnancy. If only we could all hide our problems in a cheery, oversized coat. It wouldn't fix them, but it would make them look fabulous.

Princess Diana's pregnancy style was unique in the fact that it was so unabashed and of the era. It was like a timestamp of trends so specifically '80s that you could never call it classic (think: Michael Galinsky's unearthed photos of an '80s suburban shopping mall that immediately went viral). Basically, few could recreate the princess' style today without garnering a couple chuckles but that doesn't mean Diana's maternity wardrobe wasn't iconic.

Unlike what you'd expect from a woman so highly photographed, Lady Di wasn't trying to shrink her temporarily expanding circumference. Instead, she opted to flaunt it with a myriad of ruffles, bows, shoulder pads, and oversized, billowy cuts. This mother-to-be was proud to take up space. She was, after all, carrying the future heir to the throne. She got even bolder during her second pregnancy, and according to The Diana Chronicles (via Vogue), wanted designer Jasper Conran to make looks that would highlight her growing cleavage. "She wanted to be sexy during her maternity," Conran said.

Diana's maternity style can be summed up with one dress, and that dress would be, as Harper's Bazaar described it, the "ruffled blue and white polka dot dress" that she wore while visiting the Isles of Scilly in 1982. 

Nautical fashion is a steadfast royal tradition. The Royal Museums Greenwich traced the trend's mainstream popularity all the way back to Queen Victoria, who first commissioned a child's sailor suit for the Prince of Wales in 1846. Though Princess Diana didn't invent the trend — which saw a huge resurgence in '80s prints and necklines — she may have perfected it.

Princess Diana was a documented fan of nautical looks, but her most inspired may have been the drop-waist dress she wore to watch her former flatmate, Carolyn Pride, marry William Bartholomew at Chelsea Old Church in September 1982. This wedding look ditched the trend's traditional navy and white color palette (save for the hat) and refreshed it in a rosy pink. Years later, Kate Middleton paid homage to her late mother-in-law with a nautical, drop waist dress of her own: Her 2011 Alexander McQueen look modernized the fit of Diana's dress while adopting the trend's classic colors.

Long, checkered coats have made massive comeback in 2020 in no small part due to Taylor Swift's Folklore rollout. In some of the album's imaging, the pop star dons an oversize coat not too dissimilar from the one Princess Diana wore back in the '80s. As shocking as it is to say, Swift's look found itself in the golden middle ground between Elaine Benes and the royal family; as she sang in 2019's "London Boy," she's something of "a Tennessee Stella McCartney." Yes, there is apparently a middle ground.

Unlike some of Lady Di's other clothes, the checked Arabella Pollen coat that the Princess of Wales wore during a trip to Twyn has stood the test of time. Its wearability didn't evaporate when the '80s played their last cassette tape, largely because the fitted at the waist gives it a feminine, modern cut. In 2020, it wouldn't even be strange to pair it with a beret, though Diana put an unexpected twist on a classic by opting for one made out of suede. 

In 2019, pink and red gowns became the Emmys biggest red carpet trend, but Princess Diana practically patented this Valentine's Day color palette three decades before. The Catherine Walker color block dress and coordinating Philip Somerville hat that she wore in 1989 during her official tour of the Gulf States pushed the limits of what's considered "matchy-matchy," a so-called fashion faux-pas that's transcended decades. Much like Queen Elizabeth, the princess loved a bold color palette and wasn't afraid to put the shoulder pads on and pull the whole thing off.

Catherine Walker was a staple in the People's Princess' wardrobe; The Telegraph went so far as to call her "the woman who dressed Diana best." Even today, decades after Diana's tragic death, the brand has a regular presence within the royal family. More recently, Vogue reports that the Duchess of Cambridge commissioned the Chelsea-based atelier to craft a couple of looks for her trip to Pakistan. One of them even served as a nod to something Diana wore on the very same trip in 1996.

After marrying into the royal family, Princess Diana wore plenty of — for lack of better words — frou-frou princess gowns. Of course, any gown owned by a princess is technically a princess gown, but let's go with the colloquialism. The People's Princess clearly had fun playing off the fairy tale idea of what royalty should be, and it was never more apparent than when she wore a shimmery, ruffled Bruce Oldfield dress during a trip to New Brunswick, Canada in 1983. Fortunately, this Cinderella's carriage didn't turn into a pumpkin at midnight. That'd make for a very tricky flight back to England.

Like Catherine Walker, designer Bruce Oldfield was a favorite of the Princess of Wales. According to The Daily Mail, they became close friends and his dresses garnered enough fame that one previously worn by Diana was auctioned off for £50,000 (about $67,000 USD). This didn't last forever, though. In an interview with The Sunday Times (via The Daily Mail), the designer revealed that his label nearly collapsed when the princess "took a step back from lavish events" following her divorce and stopped wearing his gowns. Without lavish events, there's really no need for a lavish dress, at least in the world before Instagram.

Princess Diana knew how to pull off a themed look. Long before Melania Trump ever scandalized the masses by donning a colonial-style hat to a Kenyan safari, Lady Di wore a military-inspired outfit to a military academy, and, as The New York Times reported at the time, donned a traditional Japanese kimono during a visit to Japan. She nailed a themed outfit, offending few and looking ever so appropriately three steps out the door to a Halloween party. Still, one of her most striking was a nautical-inspired look that she wore to visit a naval base during her royal tour of Italy in 1985.

It wasn't the Princess of Wales' pinstriped Catherine Walker dress that really sealed the deal, though the white color palette set the tone. Rather, it was her sailor hat. Yup, she wore a sailor hat to go hang out with a bunch of sailors. The only thing missing was an anchor stamped right in the middle.

Diana ultimately accessorized her ensemble with earrings that matched her engagement ring, which makes sense. According to UPI, it was a sort of "'second honeymoon' for the royal couple" and marked the first time she visited the country since her wedding four years prior.

Fans of The Crown may have noticed that Barbour jackets are a royal family staple. According to Town & Country, the company is one of "a handful to hold three royal warrants." Kate Middleton has one. Meghan Markle has one. Even the Queen has one, and she's reportedly had it for more than 25 years.

Diana, who wasn't typically photographed in casual outfits aside from some moments heading home from the gym or hanging around at home, was also a fan of Barbour. Though pairing what's essentially a hunting raincoat with pumps is a little strange, the Princess of Wales made the look work during a trip to Scotland in 1985. She was notably underdressed next to Prince Charles and his kilt, but her coat matched the weather (it was overcast) and the setting (Barbour's founder John Barbour is from Galloway, Scotland).

Princess Diana didn't abandon her penchant for chunky statement sweaters when she became a royal — and it defined her style for years to come. Decades after she first donned her Warm & Wonderful black sheep sweater, the unmistakable knit remains her most memorable fashion moment of all time. According to CNN, it's so famous that it was added to the Victoria & Albert Museum.

In an era filled with wildly bold fashion choices, Lady Di's sweater stood out because it epitomized her perspective, if only sartorially. In some sense, her fashion set her apart from the rest of the royal family, who reportedly disapproved of some of her choices like her now-priceless sapphire engagement ring (per Vogue). She was a veritable black sheep — in more ways than one, if we're going by her Netflix documentary — and unapologetic in her boldness. "She had a much more adventurous and youthful style than what we were used to in our royalty, and she took an obvious delight in clothes and wore them with terrific style," Sally Muir and Joanna Osborne, who designed the original knit, told People.

Warm & Wonderful stopped making Diana's infamous black sheep sweater in 1994, but they ended up bringing it back 26 years later in collaboration with Rowing Blazers. It's so popular that, at the time of this writing, it's sold out.