Princess Diana’s Top Five Most Expensive Wardrobe Items

Diana, Princess of Wales (1961–1997) wearing the “Black Sheep” wool jumper by Warm and Wonderful (Muir & Osborne) to Windsor Polo, June 1981 (photo by Tim Graham Photo Library via Getty Images, courtesy Sotheby’s)

Positioned at the intersection of cult of celebrity and late-stage capitalism, the auction house can be a perfect venue to showcase the jaw-dropping sums people are willing to pay for a connection to one of their icons. For every notable or notorious person — from John Wayne Gacy to Judy Garland to Joan Didion — there is an often anonymous buyer ready to throw down serious money to take home a piece of history.

Princess Diana was no stranger to the celebrity auction; only months before her death in 1997, the beloved royal donated 79 selections from her extensive and chic wardrobe to be sold in support of philanthropic causes. Interest in the famously fashionable princess’s clothing has not waned in the intervening decades, as proved last week by the record-breaking sale of a red knitwear jumper adorned with graphic white sheep (and a single black sheep as a featured front-and-center misanthrope, much like Diana herself), designed by Sally Muir and Joanna Osborne of Warm and Wonderful. Established in 1979, the brand was thrust into the national spotlight when then-Lady Diana Spencer wore one of their original designs to a polo match in June of 1981. This outing, and the ensuing media frenzy, established the princess’s habit of making bold and non-traditional fashion choices as a public figure subject to incredible media and interpersonal scrutiny. The original sweater sustained some damage that day, causing Diana’s secretary to seek its repair or replacement. Happy to replace a piece that had so greatly boosted their brand recognition, the original sweater worn by Princess Diana was stored in an attic and forgotten until March of 2023, when Osborne discovered it while looking for an old pattern. Where else to go, but to auction? While Sotheby’s likely expected the item to exceed its projected value of $50–$80K, the hammer dropped at $1,143,000 — more than 14 times its high estimate.

Though this item set two new records — most valuable item of Princess Diana’s clothing ever sold at auction, and most valuable sweater ever sold at auction, according to Sotheby’s — this is not the first time a garment worn by the iconic princess has fetched a royal sum. Here are the five highest auction results associated with Princess Diana’s clothing … for now.

1. Princess Diana’s Sheep Jumper

Sheep Sweater Front
“Black Sheep” wool jumper by Warm and Wonderful (Muir & Osborne) (1981) (image courtesy Sotheby’s)

There is great power in confirming public perception, and the sheep motif amplified Diana’s ‘Lady of the People’ title,” says Sotheby’s auction description. “The sheep pattern could be interpreted as a nod to British agricultural history; A celebration of the countryside that also lends itself to creating a sense of groundedness.” Paying more than a million dollars for that same sweater perhaps deflates some of that aura of humility, but we didn’t bring our things to auction to give the stuff away, amirite?

2. Princess Diana Ball Dress

Princess Diana Dress Front
The Princess Diana Ball Dress by Victor Edelstein (Autumn 1989) (image courtesy Sotheby’s)

The Princess Diana Ball Dress (Victor Edelstein, 1989) sold at Sotheby’s this January for $604,800. This stunning gown in intricately pleated aubergine velvet was part of the 1997 charity auction at Christie’s, which presented 79 of Princess Diana’s dresses, but its return to the auction block at the start of this year set a high watermark for demand of Diana-wear. The dress was one of Diana’s favorites, appearing in many canonical images of the princess, from a the royal portrait shot by Lord Snowdon (then-husband of her aunt-in-law Princess Margaret) in 1991 and Douglas Hardinge Anderson’s painted portrait of that same year to a photograph taken by fashion photographer Mario Testino for the 1997 Vanity Fair spread published mere months before her death.

3. Bruce Oldfield Silk Gown and Catherine Walker Evening Gown

Princess Di red silk Bruce Oldfield 182719 copy
Red Silk Bruce Odenfield (1991) and Black and Jade Catherine Walker (1991) (images courtesy Julien’s Auctions)

The Premiere Worn Bruce Oldfield Silk Gown (Bruce Oldfield, 1991) and Gala Dinner Worn Catherine Walker Evening Gown (Catherine Walker, 1991) sold at Julien’s Auctions this month for $571,500 each. Perhaps the appetite for the record-setting sheep jumper was whet by an auction at Julien’s earlier this month, in which a trio of Princess Diana’s gowns all eclipsed $500K. The red silk Bruce Oldfield number seems a little classy for the premiere of the 1991 slapstick war comedy Hot Shots, but a red carpet is a red carpet, after all, and paparazzi images capture Princess Diana exchanging handshakes with Charlie Sheen before the event. The jade Catherine Walker feels more appropriate to the context, as it was worn to a gala dinner at the Royal York Hotel in Toronto in 1991. Both gowns, and another Catherine Walker that ranks fourth on our list, were bought by businesswoman Ellen Petho at the 1997 Christie’s auction, according to Tatler.

4. Catherine Walker Custom-Made Black Velvet and Ivory Gown

Princess Di black white Catherine Walker 182717
Custom black-and-white Catherine Walker (year unspecified) (image courtesy Julien’s Auctions)

A Custom-Made Black Velvet and Ivory Gown (Catherine Walker, year unspecified) also sold at Julien’s Auctions this month, for $508,000. The final dress in the trio worn by Princess Diana to a private event fetched slightly less than the two discussed earlier, but it’s still a serious number; one assumes that Petho got a solid return on her 1997 Christie’s acquisition. Catherine Walker was one of Princess Diana’s favorite designers, creating custom designs for the royal across almost two decades, including the black dress in which Diana was buried at Althorp, her family estate.

5. Murray Arbeid Evening Gown

Princess Diana at Worshipfull Company of Fanmakers Banquet Mansion House December 1985 Tom Wargacki for Getty Images
Left: Princess Diana at Worshipfull Company of Fanmakers Banquet, Mansion House December 1985 (photo by Tom Wargacki/WireImage); right: gown by Murray Arbeid (photos courtesy Sotheby’s)

The Princess Diana Evening Gown (Murray Arbeid, 1985) sold at Sotheby’s, also this month, for $381,000. Though the sheep jumper was the belle of ball last week, this one didn’t do too badly, either. Worn twice by Princess Diana in 1985, to celebrate Prince Edward’s 21st birthday at the Midsummer Nights Ball in June and again in December to the Worshipfull Company of Fanmakers Banquet, the black, strapless velvet sheath is buttressed by a cascade of white taffeta. As recounted to Vogue in 2021, Natasha Fairweather, a university friend of Prince Edward also in attendance at the ball, was mortified to discover that she had arrived at Windsor Castle for the birthday party in the same dress, even going so far as to consult the Queen Mother for advice about the faux pas (apparently, it was deemed acceptable to remain at the party). In 2019, a Victor Edelstein gown worn by Diana while she danced with John Travolta at the White House in 1985 sold for £281,000 (~$347,000).

With so many of Princess Diana’s auction items resurfacing, these may not be the last record-shattering numbers we see for the wardrobe of one of history’s most enduring princesses.

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