The first time that Lady Diana Spencer stepped out in the black-sheep sweater (or jumper, as the British would call it) was in June of 1981. She was nineteen years old and a month away from the wedding that would transform her from a nursery-school assistant in Pimlico to the Princess of Wales. Before moving into Buckingham Palace, Diana had been living with three girlfriends in a spacious flat in Knightsbridge which her parents had bought for her; she is said to have hung a sign above her bedroom door that read “Chief Chick.” This cheeky autonomy ended almost overnight, however, once Diana and Prince Charles became engaged. From the moment she was scuttled out of her flat and into a royal car, Diana was monitored, groomed, told what to say and, more importantly, what not to say in the face of flashbulbs and prying tabloid hackettes. She wasn’t fully muzzled, but she wasn’t fully free to speak her mind, either. (Take it from Meghan Markle—no royal ever is.) So her clothes transmitted messages for her. The black-sheep sweater, which Diana first publicly wore to cheer on one of Charles’s summer polo matches, features dozens of white-wooled creatures prancing across a cherry-red background, with one lone black sheep standing out from the flock. It certainly did not carry back then the heavy, almost fated symbolism it would take on later, when Diana found herself at odds with the entire royal clan. But it did seem to telegraph a certain sense of humor about the strangeness of her newfound station: the chief chick reborn as a fledgling princess.
The two designers of the black-sheep sweater, Sally Muir and Joanna Osborne, of the knitwear label Warm and Wonderful (now known as Muir and Osborne), still do not know exactly how Diana came to own the garment—the going theory, they told me recently, over the phone, is that the mother of one of her wedding page boys gave it to her. The designers only found out that she owned one when they saw her photo in the Sunday paper. The sweater, which Diana liked so much that she wore it a second time, at another polo match two years after her wedding, became about as viral as an item of clothing could be in the era before social media, with Muir and Osborne receiving “mail bags full of post” after it appeared in the press.
The sweater appears again in the fourth season of “The Crown,” the Netflix drama chronicling the lives of the British aristocracy throughout the twentieth century, which returned last weekend. It makes its cameo three episodes in, when Diana (played by Emma Corrin, an actress plucked from relative obscurity for the part, not unlike Diana herself) is cloistered in the palace. The shot is part of a montage that shows Diana during the bizarre, whirlwind months between her engagement and her globally televised wedding. We see her in a rare moment of adolescent joy, roller-skating through Buckingham Palace’s halls while blasting Duran Duran on her Walkman; we also see her late-night binging on puddings from the palace larder, before making herself throw up in her en-suite bathroom. We witness the giddiness she feels in answering her first royal fan mail, and also the rigidity of her ballet lessons. She wears her sheep sweater (one of the only original versions left, which Muir and Osborne lent to the production) while plopped in front of the telly, watching a news segment about English schoolchildren making wedding cards for the happy royal couple. The sweater is there and gone in a flash, not the public wink that it read as in real life but a sombre, private affirmation of Diana’s gilded solitude.
The sweater wasn’t typical of Diana’s look back then. As a blushing fiancée, Diana wore a lot of puff sleeves, scallop-neck blouses, dainty Liberty florals, Laura Ashley-esque cottagecore pastels, pussy bows and ribbon ties and Peter Pan collars. The look was somewhere between a librarian and an eighties sorority girl, and it cemented her image as the supportive soubrette to her besuited husband-to-be, the worldly sophisticate in herringbone, thirteen years her senior. Post-divorce, though, Diana’s style transformed, and her wardrobe seemed to transmit a kind of carefree abandon, a hard-earned boldness born of walking away from Highgrove. She wore sharp menswear-style blazers and sleek sequinned gowns, and, in her less-formal hours, stepped out in slim high-waisted jeans, slouchy sweatshirts, and baseball caps—looks that inspire no less admiration today than they did when Diana first wore them.
Eloise Moran, a fashion writer from London who now lives in Los Angeles, runs @ladydirevengelooks, one of hundreds of Diana-appreciation accounts on Instagram, where she posts pictures of Diana’s outfits, mostly from the nineties. Moran, who is twenty-eight, is too young to remember firsthand the period her account pays tribute to. She told me that, before starting the channel, she “was not, like, super obsessed with Diana.” She gained an appreciation of Diana’s style only a few years ago, while watching a royals documentary. “It was utterly anti-establishment and against this female, princessy way of dressing,” she said. The account, with its parade of glamorous, irreverent looks (plus an image, by a British spoof artist, of a Diana lookalike flipping off the camera), appeals to a new generation eager to celebrate the empowerment narrative in Diana’s fashion choices, how her clothes symbolize a kind of wearable middle finger wagging in the face of the monarchy and the press.
This is the same younger generation of Dianaphiles that the thirty-three-year-old designer Jack Carlson is catering to with his recent reissue of two of Diana’s most iconic sweaters (including, naturally, the black-sheep number), for his preppy label Rowing Blazers. The brand, which launched in 2017 and has gained a cult fan base among celebrities (including Timothée Chalamet), makes pieces—ostentatious rainbow-stripe blazers, oversized polo shirts, and saucy corduroy and nylon hats, embroidered with phrases such as “Are You A Preppie?” and “All Is Vanity”—that ride a delicate line between worshipping the sartorial codes of élite institutions and taking the piss out of them. “If there’s one thing I hate, it’s, like, stuffiness,” Carlson, who was educated at Georgetown and Oxford, and was formerly a coxswain for the U.S. national rowing team, told me. Diana’s black-sheep sweater is the brand’s first foray into womenswear. Carlson worked with Muir and Osborne to recreate the original faithfully. (“Well, it is slightly improved,” Osborne told me. “The original had long strands that you could get your jewelry caught in.”) The sweaters, which are handmade in Portugal and cost two hundred and ninety-five dollars, went live on the Rowing Blazers site on October 8th. They sold out within twenty-four hours. “ ‘The Crown’ certainly helps, and I’ve had lots of people asking if we planned these sweaters to come out with the new season,” Carlson said. “And the answer is no! I’ve been working on this for nearly two years. If we had had any idea at the beginning of this process how much excitement there was going to be, we would have made a lot more.”
For those less inclined toward wayward livestock, Carlson has also reissued a ballsy peach sweater, originally from the brand Gyles & George, that reads “I’m a Luxury” in blue lettering on the front and, on the back, “Few Can Afford.” Gyles Brandreth, one of the brand’s co-founders, told me over Zoom, from his London home, that Diana purchased the sweater sometime in the late nineteen-eighties, from the Gyles & George shop in Kensington. “She would do her own shopping,” he said. “It was not normal for a royal, but she was not a normal royal.” Brandreth, a sprightly former M.P. and game-show host, has gone a bit viral himself lately, for posting selfies showing off his own sweater collection, including an original “I’m a Luxury.” He likes to tell the story of meeting the Princess of Wales in person, some years after her purchase. “She said, ‘Oh, I wear your jumpers!’ ” he told me. “And I said, ‘No, no, I wear yours.’ ”
On “The Crown” ’s next season, when Elizabeth Debicki takes over the role of Diana, viewers will presumably get to see the show’s homage to her more liberated, post-divorce style. In the meantime, the wedding episode recreates Diana and Charles’s infamous engagement interview, during which a journalist asked the couple if they were in love and Charles brusquely answered, “Whatever ‘in love’ means.” The real Diana later said that this comment “traumatized” her and made her second-guess her nuptials—that and her discovering that Charles never intended to stop seeing his former flame, Camilla Parker Bowles. It is strange, watching the show’s wrenching account of Diana and Charles’s crumbling union, to know that, years later, her heartbreak would be converted into a kind of girl-power shorthand that shoppers could consume. Before she was a luxury few can afford, Diana certainly paid a price.
