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When the Lord Chancellor announced Prince Charles’s engagement to Lady Diana Spencer on 24 February 1981, American Vogue promptly commissioned a table laying out the betrotheds’ “cars, clubs, income [and] endearing mannerisms.” Charles, readers learned in the May 1981 issue, loved Aleksandr Isayevich Solzhenitsyn’s works on the Gulag, was nicknamed Action Man and Golden Eagle, counted Verdi as his favorite composer (with a particular fondness for La Traviata), and habitually wore both Turnbull & Asser shirts and Penhaligon’s cologne. Diana, on the other hand, was fanatical about Not the Nine O’Clock News, known to her friends as “Shy Di,” and was given to “endearing sideways glances”.

The starkest difference between the two, however, was their romantic history. Historian Andrew Barrow listed out 23 of the 32-year-old Charles’s former paramours for Vogue, including Princess Marie Astrid of Luxembourg, Anna “Whiplash” Wallace, and Diana’s sister Lady Sarah Spencer. Precisely no one, however, was name-checked as a former love interest for the 19-year-old Diana, who had been selected as the royal bride in no small part because of Buckingham Palace’s insistence that Charles marry a virgin. The Queen Mother, in particular, felt the “sweetness and modesty” of “the Spencer girl” made her an ideal candidate for the role of Princess of Wales.

Diana was a startlingly cosseted teenager in the Jilly Cooper age, a waif whose most notable academic achievements included the Palmer Cup for Pets’ Corner at Sevenoaks (she was devoted to her guinea pig, Peanuts), and who kept a toy frog on the hood of her Mini Metro, a reminder that she would one day meet her prince. It’s difficult to blame the much more experienced Charles for struggling to perceive her as a serious life partner—“She is exquisitely pretty, a perfect poppet… but she is a child,” he reportedly said during their all-too-brief courtship—and her air of girlish innocence was only emphasized by her clothes.

Prior to her engagement, it was Diana’s mother, Frances Shand Kydd, who selected her wardrobe for her, which meant she frequently wore dowdy garden-party hats from milliner John Boyd and blousy, floral dresses courtesy of Donald Campbell. It would be British Vogue who came to Diana’s sartorial aid—particularly its fashion editor, Anna Harvey. “The first time I met Lady Diana Spencer was in 1980, in the editor’s office,” Harvey recalled in a tribute in the October 1997 issue. “Her sisters had worked at Vogue, and we thought we might be able to help with her image. I’d called in far too many clothes because I had absolutely no idea of the kind of thing she liked. By the time she arrived, I was shaking like a leaf, but I took one look at her and thought, This isn’t going to be too difficult after all.”

“Black to me was the smartest colour you could possibly have at the age of 19,” Diana later explained of wearing the Emanuels’ gown. “It was a real grown-up dress.”

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For an early Vogue portrait taken by Snowdon before Charles had formally proposed, Harvey selected a rosy silk chiffon blouse for Diana to wear by the Emanuels, whose offices were just down the road from Vogue House on Mayfair’s Brook Street. The designers’ studio—then a haunt for celebrities ranging from Bianca Jagger to Lulu—would become a haven for “Shy Di” in the months that followed, when she began to feel less secure in the fairytale she was supposedly enacting. In that era, whenever she tried to choose her own looks without Harvey and her cohort’s input, it backfired. Case in point: for the landmark BBC interview to coincide with Buckingham Palace’s engagement announcement, Diana had gone shopping at Harrods with Frances, plucking a royal-blue Cojana London suit and pussy-bow blouse off the rack of the Knightsbridge store. Even the most fawning media outlets had to admit it made her look matronly, old-fashioned, and—to quote Tina Brown—like a “Sloane on the frontispiece of Country Life.”

The above look was a marked departure from the suit Diana had worn for a recent BBC interview.

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Said outfit only deepened the world’s impression of Diana as naive and childlike. “Shy, innocent, modest, retiring, demure, and coy, the girl next door… These are just some of the labels which have stuck to Lady Diana Spencer during the intense speculation leading up to yesterday’s announcement of her engagement to Prince Charles,” declared The Times. “It was for some of these reasons that she has seemed to many people such an eminently suitable choice to become the first Princess of Wales since 1901 and the future Queen of England… At the age of 19, she is young enough not to have been seriously involved with other men—something that is said to have been an important consideration to Prince Charles and his advisers… Her youth is in contrast to some of the older and more independent women whom Charles has previously accompanied.”

Prudence Glynn was one of the noted fashion journalists to criticise Diana’s gown: “Nobody wears a strapless dress to an occasion on which she will be seated most of the time. Why? Because you look as though you are sitting in a hip bath, silly!”

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Across the Atlantic, the New York Times echoed the words of its London counterpart in the wake of the BBC interview, reporting that Diana “loves children, avoids nightclubs and stylish parties, and blushes engagingly whenever she is sighted by the posse of press photographers who have been pursuing her for months.” “She is described by her friends as gentle and shy,” the story continues. “During the ordeal of pursuit to which Fleet Street reporters have subjected her in recent months, she has shown good humor and patience, although once, surprised by photographers at the wheel of her red Mini Metro, she burst into tears.” Ominously, the piece concludes with a quote from Diana: “I know it’s just a job they have to do, but sometimes I do wish they wouldn’t.”

Princess Grace of Monaco was also in attendance at Goldsmiths’ Hall that night. When Diana confided in her about her fears for the future, Grace simply replied: “Don’t worry; it will get a lot worse.”

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Still, Diana would soon realize that she could use said Fleet Street reporters to her own ends. The future royal had already twigged that Charles’s affections were divided; famously, it’s during this period that she returned to Clarence House to find a letter from Camilla Parker Bowles congratulating her on her engagement—days before anyone outside the Windsor clan was meant to have known about it. Yet the world had underestimated the lengths to which “Demure Di” would go in order to hold Charles’s attention. (As Jasper Conran would depressingly recall in The Diana Chronicles: “No matter what you were making for her, the question was always, ‘Will my husband think I am sexy in this?’”)

And so, in what would become a pattern throughout her 15 years in the royal family, Diana set about bursting the English-rose bubble with her fashion choices. For her first public date with her fiancé in the City of London one cool night in March, she asked the Emanuels to make her something suitable, but when she dropped by their studio to collect it, she clocked a dress that Alvin Stardust’s wife, Liza Goddard, had previously worn to a charity event, and asked to try that on instead. “It felt so different to anything she’d worn before,” Elizabeth Emanuel recalls now of the strapless ruffled gown with a plunging heart-shaped bodice. “She looked so grown up, like a movie star, and she loved the idea of breaking the mold.”

In many ways, the dress was all wrong for the evening’s musical recital at Goldsmiths’ Hall. Royals are notoriously meant to avoid black unless in mourning, for starters—and then there was the question of Diana’s “décolletage,” as the press called it. “Lady Diana wore a low-cut gown, well off the shoulder, and there were audible admiring gasps,” reported a positively giddy BBC journalist. (“I was quite big-chested then, and they all got frightfully excited,” Diana deadpanned in her tapes for Andrew Morton.) “Prince Charles, all but forgotten for the moment, seemed amused by the interest in his fiancée’s attire,” The New York Times declared. “After escorting her past a crush of photographers, he called back, ‘Have all the fashion writers finished?’”

The fashion writers were just getting started—and so was Diana. She would later claim to have been affronted by the press’s reaction that night, telling Morton: “I remember my first [royal] engagement so well. So excited. Black dress from the Emanuels and I thought it was OK because girls my age wore this dress. I hadn’t appreciated that I was now seen as a royal lady, although I’d only got a ring on my finger as opposed to two rings… It was a horrendous occasion.” It can’t have been wholly horrendous, though, as within a month, she’d brought the dress back to the Emanuels; she needed it altered to fit her new, slimmer frame, she said—and, yes, she had every intention of wearing it again.