The Star of Sotheby’s Fashion Icon Auction 

Bidders, start your engines! Sotheby’s is hosting an online auction, titled “Fashion Icons,” opening Aug. 31 and closing Sept. 14. Although this auction features many noteworthy pieces from influential people, or pieces that captured a cultural moment in time, the item we’re most excited about is a sweater owned and immortalized by the late Diana, Princess of Wales. It’s the cherry red Black Sheep sweater, which carries an estimate of $50,000–$80,000, and will be on view at Sotheby’s New York during the second week of the online auction.

We love an iconic piece of fashion history. This one is top-tier, right up there with Audrey Hepburn’s little black dress from Breakfast at Tiffany’s, Jacqueline Kennedy Onassis’ sunglasses, Theda Bara’s 1917 Cleopatra costume with its snake-motif breast plates or Jayne Mansfield’s low-cut dress worn to a dinner honoring Sophia Loren. You know the one. 

Side note: The photos from that particular evening in 1957 capture Loren’s side-eye in all of its glory. The actress later explained, “Paramount had organized a party for me. All of cinema was there, it was incredible. And then comes in Jayne Mansfield, the last one to come. For me, that was when it got amazing … She came right for my table. She knew everyone was watching. She sat down. And now, she was barely … Listen. Look at the picture. Where are my eyes? I’m staring at her nipples because I am afraid they are about to come onto my plate. In my face you can see the fear. I’m so frightened that everything in her dress is going to blow — BOOM! — and spill all over the table.”      

But we digress. The Black Sheep sweater, which theoretically could soon be yours, is one of the most recognizable pieces worn by Princess Diana. Says Sotheby’s: In June of 1981, a newly engaged Lady Diana Spencer wore a red sweater dawned with a whimsical black and white sheep motif: one of the first designs by Sally Muir and Joanna Osborne of “Warm and Wonderful” knitwear established in 1979. The newspaper coverage in 1981 was the advertisement of a lifetime and one Muir and Osborne would later accredit as the stratospheric launch of their small business.

After Diana damaged the sleeve of her beloved sheep sweater, Muir and Osborne were surprised to receive a letter from Buckingham Palace outlining the damage and enquiring whether Warm and Wonderful might be able to repair or replace the sweater. Naturally, the company immediately knitted a new one and delivered it to the Palace. Not long after, another royal missive arrived. It was an effusive thank-you letter sent by Oliver Everett, private secretary to the Princess of Wales.   

Diana wore the sweater beautifully again in 1983, with crisp white painter jeans. Remember those? Multiple pockets and hammer loop? She styled it, naturally, with the requisite ’80s big white collar and pussy bow-style tie and wore it to one of Prince Charles’ polo matches. Because the marriage was already on the rocks, some sartorial speculation suggests that the choice was intentional, telegraphing to the world her feelings of being an outsider; a royal black sheep.  

In 1993, the Victoria and Albert Museum acquired one of the sweaters for its permanent collection. The Warm and Wonderful company stopped making the sweater in 1994, but the Black Sheep never left the global sartorial vernacular. Among a certain subset, it’s something of an obsession. 

These days, Rowing Blazers offers a facsimile of the Black Sheep Sweater (men’s and women’s styles), based on the original design, for $248, or less than 1/200th of what Sotheby’s anticipates the original will sell for. 

Of course, there’s no substitute for the original’s cred: Cynthia Houlton, Sotheby’s global head of fashion and accessories, said in a statement that “this exceptional garment, meticulously preserved, carries the whispers of Princess Diana’s grace, charm and her keen eye for fashion.” •