Princess Diana’s “Black Sheep” Sweater and Michelle Obama Gown to Sell With Sotheby’s

The inaugural Fashion Icons sale from Sotheby’s will feature couture items from figures such as Princess Diana, Michelle Obama, and Madonna. Leading the catalog is Princess Diana’s “one black sheep” sweater. Made of red knit wool with a repeating pattern of white sheep, the iconic sweater is defined by a single black sheep standing out from the crowd in the fourth row. Princess Diana first wore this sweater in 1981. At the time, she was engaged to King Charles III (then a prince). Sotheby’s notes that the sweater came from Diana’s “age of innocence,” before she fully embraced the power of her wardrobe to communicate and influence. The original sweater, which is available with Sotheby’s, was damaged and returned to the Warm and Wonderful knitwear manufacturer. It languished in attic storage until being rediscovered earlier this year. 

Also available in this sale is an evening gown worn by Princess Diana twice in 1985. This Murray Arbeid gown is made of black velvet and a white taffeta mermaid silhouette. The dress attracted attention during one event when another guest unintentionally wore the same gown; Diana reportedly handled the near-faux pas with grace and humor. A vintage dress worn by Michelle Obama to the “Christmas in Washington” broadcast taping in 2010 is also available. Made in the 1950s by American fashion designer Norman Norell, this black silk and lace dress was the first vintage gown worn by a First Lady to a public event. Kate Winslet’s Alexander McQueen dress worn to the 1998 Academy Awards, a 1910s wedding veil worn by Madonna to a Vanity Fair cover shoot in 2023, and a selection of Hermès bags are available as well. Visit Sotheby’s to view the complete Fashion Icons catalog and register to bid.