PRINCESS DIANA is burned into our collective memories as glamorous and begowned—who can forget the black, off-the-shoulder Victor Edelstein dress she wore to twirl with John Travolta at a Reagan-era state dinner? But, as a source of style inspiration for us commoners, dressed-down, off-duty Di endures far more accessibly. “Her daywear was more affordable and easily imitated,” said Isabella Coraca, assistant curator at Historic Royal Palaces, the charity behind the current Kensington Palace exhibit, “Diana: Her Fashion Story.”
Unregal outfits like her sweatshirts over bike shorts are getting play with a generation newly interested in the 1980s and ’90s. After Off-White designer Virgil Abloh tacked photos of that combo on his inspiration board for spring 2018, throwback cycling shorts found their way onto the Off-White runway. For a Diana-approved option that won’t make you feel like you’re headed to Jazzercise, look to the sort of punchy cropped pants she wore as a 25-year-old at Highgrove, the royal family country home outside London, in 1986 (pictured).
According to Elizabeth Angell, digital director of Town & Country magazine, which exhaustively covers the royal family, the English-rose-colored gingham and the princess’s easy smile in this photo speak of “Diana’s sunny, optimistic early years—when she was injecting a kind of sweet, girlish charm into the staid machine of the royal family.”
The magenta hue of her pants couldn’t be more ’80s, but the preppy print and above-the-ankle cut have a classic Jackie O.-in-Capri vibe for India Hicks, a bridesmaid in the princess’s 1981 wedding and founder of an eponymous fashion and accessories brand. “It’s very much a movie-star moment, and yet everyone we know has probably got a pair of cropped pants,” said Ms. Hicks. “Although Diana drove fashion trends, I think [her taste] was, at heart, pretty timeless.”
More than three decades later, such cheeky statement pants still reign unchallenged. J.Crew reliably carries a black-and-white gingham version, while Chloé ventures into galloping horse prints; Etro boasts a trippy wavy pattern and Closed offers smart, checked options. Cropped, printed pants are not only unabashedly fun, they’re “perfect for women on the go,” said Closed co-owner Gordon Giers, who recommends breaking up the pattern with a denim shirt or a wide-wale corduroy blazer or styling the trousers with a matching top.
While Diana’s pink sweatshirt is better left in the ’80s, her matchy styling syncs up with prevailing trends today. Clara Cornet, creative and merchandising director of Paris department store Galeries Lafayette, likes pairing bright pants with a cashmere knit top of the same hue. “It’s all about monochrome,” she said. For Ms. Hicks, who copped to wearing a pair of A.L.C. cropped pants when we spoke, the trousers hit a sweet spot of casual elegance—“a step up from the jean”—while transitioning without complaint from flats to boots in the tricky micro-season of early fall.
Indeed, don’t be fooled into writing off cropped pants as a just-for-spring thing. “There’s something about fall foliage that makes you want to dress like you’re strolling through a boarding-school campus,” said Ms. Angell. Or, like Princess Diana, in her felicitous pink pants on the Highgrove grounds, “headed to an English country weekend.”