(London) A red sweater adorned with a flock of sheep worn by young Princess Diana is expected to sell for more than $50,000 (nearly C$66,000) at auction.

The playfully patterned wool sweater with a single black sheep amidst white sheep headlines Sotheby’s ‘Fashion Icons’ online sale in September.

Lady Diana Spencer, 19, was pictured in the garment at a polo match in June 1981, shortly after her engagement to Prince Charles, then heir to the British throne.

Diana was already becoming a fashion icon – and one of the most photographed women in the world – and that moment gave designers Sally Muir and Joanna Osborne a big boost, who made the sweater for their small brand of Warm knitwear

A few weeks later, Ms Muir and Ms Osborne received an official letter from Buckingham Palace explaining that Diana had damaged the sweater and asking if it could be repaired or replaced. The original has been returned, showing damage to a sleeve that the designers believe may have been caused by Diana’s diamond and sapphire engagement ring.

A new sweater was knit and shipped, and Diana was photographed wearing it with white jeans and a black ribbon tie to an event in 1983.

Some have speculated that Diana liked the “black sheep” motif because she felt like an outsider in the royal family. Emma Corrin sported a line as young Diana in season four of The Crown.

Warm

Cynthia Houlton, global head of fashion and accessories at Sotheby’s, said “this exceptional garment, meticulously curated, carries whispers of Princess Diana’s grace, charm and her keen sense of fashion”.

The sweater, which is estimated to be priced at US$50,000-80,000 (approximately C$66,000-105,000) will be on display at Sotheby’s New York showroom from September 7-13. Online auctions open August 31 and end September 14.

The record for a Diana memorabilia is US$604,800 for a ball gown designed by Victor Edelstein, which was sold by Sotheby’s in January.