Today marks what would have been Princess Diana’s 56th birthday. The late royal will always be remembered for her grace, her charm, and her beauty, though her style remains a significant part of her legacy. The world will never forget images of Diana in her David Emanuel wedding dress, encrusted with 10,000 tiny mother-of-pearl sequins and pearls, with a train spanning 25 feet—the longest in royal history. More than 17 million people tuned in to watch her wed Prince Charles at St. Paul’s Cathedral in 1981. But it wasn’t long before the new bride, the one previously found in prim blouses and pastel ruffles, transformed into the sleek, sophisticated woman the world thinks of today.
There were specific outfits for trips abroad, each fashioned to pay homage to the host nation. When she traveled to Saudi Arabia in 1986, she chose a dress decorated with gold falcons—an emblem of the Middle Eastern nation. But for all this pomp and circumstance, a look back at Diana off-duty reveals a new aspect of her style—and it’s as relatable and wearable now as it was the first time around.
Take, for example, a throwback photograph of Diana dashing into the Harbour Club in spandex shorts and a Harvard sweatshirt; the look is right in line with today’s athleisure trend. The same could be said for the nubby gray sweatpants she wore in 1989 while dropping her sons off at Wetherby School in London. (The cowboy boots, in particular, have that anything-goes Sloane Ranger ease she made standard). And who could forget that velvet LBD she wore in 1994? Just as a documentary about her husband’s infidelities aired, a lithe and leggy Diana floated into a Serpentine Gallery benefit wearing a body-conscious cocktail dress by Christina Stambolian. The next day, tabloid front pages were devoted not to Charles’s televised confession, but to photos of a confident and chic Diana.
The common thread between each turn is clothing that suited her, regardless of the dictates of fashion—a feat which was all the more impressive in the trend-centric ’80s and ’90s. Here, in honor of the icon’s everlasting style, are five ways to channel Princess Diana off-duty, on her birthday and beyond.
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