Princess Diana’s Iconic Sheep Sweater Is Reincarnated As Sperry Sneakers

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Twenty-five years after her death, Princess Diana’s style is still in vogue (sometimes literally in Vogue). Lately, it is William and Harry’s mum’s penchant for off-the-clock normcore knitwear, specifically the infamous black sheep jumper (that’s English for sweater) she wore in the Eighties, that is earning revisionist reviews by editors, being rediscovered by a younger generation obsessed with The Crown and the Kate Middleton-Meghan Markle era of royalty, and sparking nostalgic fashion trends.

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The latest American designer to jump on that bandwagon is Sperry, which has just released a sneakers collaboration with Warm & Wonderful, the heritage British brand behind the original top.

sperry sheep shoes
sperry sheep shoes

Sperry x Warm & Wonderful Sneakers

Price: $90

Buy Now

The unisex Sperry x Warm & Wonderful line applies the bovine motif to the Cloud CVO, Sperry’s original canvas deck sneakers, in four colorways: Diana Red, Bowie (yes, that David Bowie, as the singer was also a W&W supporter) Blue, Original Green, and Primrose Hill Pink.

The kicks, available for $90 on Sperry.com, come almost two years to the month after New York-based Rowing Blazers released a menswear collection inspired by the people’s princess that featured authentic recreations of two of her most memorable pullovers including the black sheep print and the “I’m a Luxury … Few Can Afford” design.

Although the animal article has been knocked off many times since Di sported it, most famously in Lanvin-vest form by Harry Styles in 2019, it was the first time accredited authentic versions were available outside of eBay (where they routinely fetch $900), as Warm & Wonderful had retired the low-key look in 1994. Di’s enduring influence has kept the sweater, as well as vest and zip-up fleece versions, in stock.

Diana, Princess of Wales (1961 - 1997) wearing 'Black sheep' wool jumper by Warm and Wonderful (Muir & Osborne) to Windsor Polo, June 1981. (Photo by Tim Graham Photo Library via Getty Images)
Diana, Princess of Wales (1961 - 1997) wearing 'Black sheep' wool jumper by Warm and Wonderful (Muir & Osborne) to Windsor Polo, June 1981. (Photo by Tim Graham Photo Library via Getty Images)

Warm & Wonderful Sheep Sweater

Price: $295

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The sneakers, meantime, are available in sizes 4 to 13. Though the designs are unisex, the shoes are in men’s sizes (for women’s sizing, subtract 1.5 from the listed size online).​​

Prefer a non-sheep-branded shoe? Sperry also makes the CVO sneaker in neutral colors and materials, starting at $69.95.

“Paul Sperry designed the CVO in 1935 and the shoe has been a favorite of style leaders for 87 years,” Elizabeth Drori, Sperry’s chief marketing officer, tells Rolling Stone. “Warm & Wonderful’s black sheep pattern, made famous by Princess Diana, one such iconoclast, as she telegraphed her outsider image to the world is the perfect update to a timeless shoe.”

The sweater, which the princess wore to a polo match in 1980 while still just engaged to then-Prince Charles, saw another bump in popularity when it appeared on Emma Corrin in the fourth season of The Crown, which also returned last week.

In this day and age of prince-penned memoirs, prestige film and TV projects, royal documentaries, and revealing Oprah interviews, it can be hard to comprehend why an article of clothing that could easily be written off as PTA mom-worthy, or, worse, novelty wear, plays such an important part of Diana’s fashion journey and eventually became part of the Victoria & Albert Museum’s permanent collection.

It is crucial to remember that Diana’s lips were never allowed to be that loose and historians believed that she often used her wardrobe to communicate her rebel status among the royals, her of-the-people-ness, her discontent in her marriage, and eventually her revenge stage post-divorce. We dare you to find a greater outsider symbol than a singular black sheep among a herd of white ones.

The Princess Diana-inspired Sperry x Warm & Wonderful line is available to shop online now at Sperry.com.

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