The words “shocking” and “fashion” are not natural bedfellows for the British royal family, who employ clothes for diplomacy, symbolism and visibility. There is nothing scandalous about the Queen’s signature color-blocking, designed so that her subjects can see her petite frame on public engagements. Nor the Duchess of Cambridge’s dress coats, which lend a certain degree of predictable polish to photo opportunities.
But before Kate Middleton became a Cambridge, she was a Sloane Ranger with a penchant for what Mayfair’s Mahiki club had to offer. Diana, Princess of Wales, too, was not immune to killer party dresses that got the paparazzi flashing. How could they be? Princess Margaret had paved the way for them.
From the eveningwear that was a hop, skip and a jump away from royal protocol, to the distressed denim jeans that found their way into The Firm by way of Meghan Markle, here are the most eyebrow-raising looks to come out of the palace.
PA1/9The ripped jeans
When Prince Harry and Meghan Markle made their first public appearance together at the 2017 Invictus Games, the world zeroed in on one thing: the frayed slash on the left knee of the Suits star’s Mother Denim skinnies. Yes, we’d witnessed spray-on denim before, thanks to the Duchess of Cambridge’s Zara obsession, but this was a new one. Even better, she had royal style watchers Googling “French tuck”, thanks to her Misha Nonoo boyfriend shirt.
PA Photos2/9The revenge dress
Princess Diana’s decision to wear her Christina Stambolian LBD to the Serpentine summer party in 1994—the same night as Prince Charles’s infidelities aired on television—was entirely impromptu. She had planned to wear Valentino, but a change of heart and a desire to “look a million dollars” saw her throw caution to the wind and take a punt on the off-the-shoulder option. The image of Diana—pearl choker on, smile set—is now ingrained in the public psyche. Touché.
Photo: Getty Images3/9The charity catwalk number
Read Tina Brown’s The Palace Papers to find out what Prince William really thought of the sheer dress Kate Middleton wore on the makeshift runway at a well-publicized St Andrews fundraiser, but here’s the lowdown. Originally conceived as a skirt, which cost fledgling designer Charlotte Todd £30 to make, the ribbon-trimmed lace bandeau later sold for £125,000 at auction. Kate, with her corkscrew ringlets and silver nail polish, owned it.
Steve Back/Getty Images4/9The diaphanous skirt
A young Lady Diana Spencer got an early taste of the public scrutiny she would face after marrying into the Windsor clan when a photographer snapped her outside of her workplace, the Young England Kindergarten in Pimlico, in 1980. Although the future princess’s outfit seems demure by today’s standards, her long skirt—which became momentarily translucent during a burst of sunshine—caused a scandal when the images hit the newspapers. “I don’t want to be known as the girlfriend who had no petticoat,” Diana reportedly told her then-boyfriend Charles after the fact—before quickly learning that when it comes to royal fashion, nothing can be left to chance.
Chris Jackson/Getty Images5/9The Matrix-style sunglasses
Like the Queen, Princess Anne’s wardrobe is defined by functional, classic pieces—no frothy Dior ballgowns here—but every so often, the Princess Royal will throw us a sartorial curveball. Take her beloved Adidas sunglasses, which set Twitter alight after she wore the Team GB style to the Chelsea Flower Show in 2018. Anne has actually owned the Matrix-style frames since at least 2008, when she wore them to a dressage test during the Beijing Olympic Games.
New York Daily News/Getty Images6/9The Met Gala slip
Diana made her only appearance at the Met Gala in 1996, a few months after her divorce had finally been made official. True to form, the royal used the fundraiser to make a sartorial declaration of independence, wearing a navy Dior slip that violated all manner of royal protocols to chair the event with Vogue’s Liz Tilberis.
Bettmann7/9The Poltimore tiara
When it came to her wedding jewelry, Princess Margaret broke with tradition during her marriage to the Earl of Snowdon in 1960. While it’s customary for Windsor brides to wear a family heirloom, Margaret purchased her Poltimore tiara from Christie’s in 1959. Designed by Garrard in 1870, its previous owner, Lady Poltimore, had worn the headpiece to the coronation of King George V in 1911. Today, the Poltimore is best remembered as the tiara that Margaret wore when she posed nude in the bathtub of her Kensington apartment for her husband in 1962. Released by Snowdon after Margaret’s tragically early death in 2002, the royal family has since had the image withdrawn from view.
Tim Graham/Getty Images8/9The pointed knitwear
Diana wore this cozy Warm & Wonderful jumper—depicting a single black sheep amongst a wooly white flock—to a polo match in 1981, just a month before her wedding to Charles. It’s only years later, after rumors of their strained marriage began to circulate, that the jumper made headlines, though—with the newspapers taking it as evidence that Diana had never truly felt like she belonged among the Windsors. Today, the design rests in the permanent collectsion of the V&A, with the brand Rowing Blazers issuing their own version of the design back in 2020 after Emma Corrin wore a replica in The Crown. Diana’s other controversial knitwear moment? Her choice of a salmon Gyles and George knit bearing the slogan “I’m A Luxury Few Can Afford” to take photos with a young William and Harry.
Max Mumby/Indigo/Getty Images9/9The roller-disco look
In the years immediately following her graduation from St Andrews, the Duchess of Cambridge regularly got papped heading into London nightclubs like any other twenty-something, with Boujis in Kensington and Mahiki in Mayfair among her favorite watering holes. It’s the outfit she wore for a midnight roller disco in Vauxhall that garnered the most headlines, however. The then 26-year-old Kate paired teal sequins with mustard hot pants and fuchsia legwarmers to cruise around the Renaissance Rooms, with the goal of raising funds for a children’s hospital in Oxford.
