Princess Diana’s ‘Black Sheep’ Sweater Just Sold for Over $1 Million. Here’s Why It’s So Significant

A month before she donned her iconic bridal gown—and years before she made headlines in her notorious "revenge dress"—Diana, Princess of Wales, donned a red, sheep-print sweater that became an indelible metaphor for her life as a royal. The Warm & Wonderful brand piece, a wool intarsia-knit with a pattern that features a single black sheep amid rows of white ones, was first worn by Diana to a 1981 polo match when she was 19 years old and just weeks away from marrying the future King Charles.

The sweater, which was rediscovered last spring in the attic of one of the Warm & Wonderful founders, just sold at auction for the first time. On Sept. 7, Sotheby's New York put the piece up for auction as part of their inaugural "Fashion Icons" event, where it was available for bidding until Sept. 14. While the sweater originally retailed in the '80s for about $50, Sotheby's initially estimated it would sell for $50,000 to $80,000. The winning bid was a whopping $1.1 million, which set a new record for any article of clothing worn by the late princess. The sale surpassed the existing record set in January of this year, when Diana's purple Victor Edelstein gown sold for $604,800. The sheep knit also broke the record for the most valuable sweater ever sold at auction, previously held by Kurt Cobain’s green cardigan from Nirvana’s MTV Unplugged concert, which sold for $334,000 in 2019.

Though the sweater's sheep pattern appears lighthearted and even whimsical, many have found meaning in the 'black sheep' design, given how Diana ultimately struggled to find a comfortable place within the royal family. Known as "the People's Princess," Diana was beloved by the public for breaking with the institution's fussy conventions, but stories about her struggle to conform—and the family's inability to accept her—have become as much a part of Diana's mythos as her philanthropic work and keen sense of style. For Cynthia Houlton, Sotheby’s Global Head of Fashion & Accessories, the sweater embodies just why Diana and her differences still resonate with people today.

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"She's a truly unique person who's remembered for who she was and the work she did—and not just how beautiful she was or what she wore," Houlton says. "When we think of the black-sheep motif, at one point it might have been considered a negative thing to be different from the rest of the flock. But today, it's OK to be unique and to stand out in the crowd. I think she probably had some feelings that she was like that black sheep—very different in the sea of the Royals, who were very much the same."

The sweater seemed to be important to Diana, whose assistant wrote to Warm & Wonderful founders Joanna Osborne and Sally Muir following the 1981 polo match to tell them that it was damaged and asking if it could be repaired or replaced as Diana "like[d] it very much." Osborne and Muir opted to replace the piece, putting the damaged one in storage, where it was forgotten until it was discovered last year in Osborne's attic, folded into an old quilt in a box of similar sweaters. A detached cuff helped confirm that it was Diana's original.

"It was crazy," Osborne says. "We thought we had lost it."

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Diana's fashion has long been a source of admiration, emulation, and almost obsessive fascination. Considered to be the most photographed woman in the world while she was living, Diana knew well the power of presentation and used her personal style to both practice fashion diplomacy at home and abroad and to skillfully express herself despite the restraints of royal life. The fact that she rewore the sweater (the replacement sent by Muir and Osborne) to another polo match in 1983 after the discomforts of her royal life had set in must be read as intentional. On the second wearing, she even styled it in a more sophisticated—and more conscious—way, with a white collar and black ribbon tie completing the look and drawing attention to the lone black sheep.

For Houlton, Diana's decision to wear the sweater again signals that it held particular significance for the princess. "By the time it was 1983, she was very aware," she says. "Because she was followed everywhere and constantly photographed, her choices were very conscious—she used fashion as a way to express who she was."