As Princess Diana’s ‘black sheep’ sweater is to be auctioned, a look back at her ‘rebellious’ fashion choices

For some it may be incredible to think that a sweater once worn by the late Princess Diana could fetch up to £70,000 when it goes up for auction later this year, but for someone who epitomised what a fashion icon is, I don’t find it surprising at all. The sweater in question is known as the ‘black sheep’ sweater and was first worn by Princess Diana when she was Lady Diana Spencer and engaged to King Charles, the then Prince of Wales. 

The then Lady Diana Spencer wore the sweater to a polo match in 1981 and it was created by Sally Muir and Joanna Osborne and their knitwear label Warm & Wonderful. In the press release the designers said the following: “Much to our amazement, the first we knew of Lady Diana Spencer wearing the sweater was when we saw her on the front page of one of the Sunday newspapers,”

 The designer duo also said that“Her influence was impactful almost immediately thereafter, leading to a surge in sales and public awareness of our small label, for which we will be forever grateful,” 

According to CNN, “A few weeks after Diana’s first outing with the garment, Muir and Osborne received a letter from Buckingham Palace informing them that Diana had damaged her beloved sheep sweater (a small tear in one of the cuffs is visible in images supplied by the auction house) and politely requesting either a repair or replacement, according to Sotheby’s”

Muir and Osborne sent Princess Diana a new sweater as a replacement after Buckingham Palace returned the original sweater. Now, as to what happened to the original sweater, it was rediscovered by the designers in their attic in March of this year. 

The original ‘black sheep’ sweater is going to feature in Sotheby’s Inaugural Fashion Icons Sale in September and could fetch up to £70,000. Over the years, there has been much speculation about ‘hidden meanings’ when it came to the fashion choices Princess Diana made and this ‘Black Sheep’ sweater is no exception. 

CNN wrote that “The media have for a long time speculated over potential hidden meanings in Diana’s clothing choices, and in this instance, the release says the sweater prompted speculation about whether the princess felt a connection to the lone black sheep because of her complex relationship with the royal family. Others simply interpret it as a celebration of Britain’s countryside and agricultural history.”

Although I believe wholeheartedly that Princess Diana made deliberate and sometimes rebellious fashion choices over the years, I think that her choice of the ‘black sheep’ sweater in 1981 was an innocent choice. After all, she was newly engaged, and her ‘complex’ relationship with the royal family only developed much later on. 

PeopleWorld takes the opportunity to look back at some of Princess Diana’s deliberate and sometimes rebellious fashion choices over the years.

The ‘Travolta’ dress in 1985

Princess Diana wore a Victor Edelstein dress when she danced with actor John Travolta at the White House in 1985. At the time it was seen as quite daring because of the off-the-shoulder style. It was part of an auction by Kerry Taylor Auctions in 2019,, but Historic Royal Palaces (HRP) an independent charity reportedly bought it outside of the auction for £264,000. 

‘The Revenge’ dress in 1994

On the day that King Charles, then Prince Charles, admitted that he had committed adultery on national television, Princess Diana stepped out in a ‘LBD’ that hs become known her as the ultimate  ‘revenge dress.’ The dress in question was an off the shoulder black dress by Christina Stambolian that she wore to the Serpentine Gallery in London and it created maximum impact. Princess Diana knew exactly what she was doing when she stepped out of the car as she looked simply incredible. 

It is believed that the Christina Stamolian dress had actually been commissioned three years previously to the Serpentine Gallery event, but it was deemed ‘too daring’ for the time.

The Dior dress at the Met Gala in 1996

Just like her ‘revenge’ dress in 1994, Princess Diana’s Dior dress that she wore to the Met Gala in 1996 was seen as ‘daring.’ It was a lingerie inspired silk slip dress in midnight blue, or navy as it is better known. 

Princess Diana had just finalised her divorce from the then Prince Charles, and the Dior dress was seen as a bold new fashion choice by the Princess to demonstrate that she was embarking on a ‘new life’ away from the royal family.

When is the sale taking place?

The ‘Black Sheep’ jumper is set to headline Sotheby’s inaugural Fashion Icons sale this September, with online bidding open from 31 August through 13 September. This will take place during New York Fashion Week and will be displayed in New York from 7 September.