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Why Princess Diana’s Style Is More Relevant Than Ever

25 years after her death, Diana’s off-duty looks endure

This week marked the anniversary of Princess Diana’s tragic death, and while it’s been a long 25 years since she was with us, her presence is always felt through the touching gestures of her sons, William and Harry. In fact, this week Harry and Meghan marked the day by visiting a Los Angeles preschool for at-risk children, where they helped the kids plant Diana’s favourite flowers, forget-me-nots.

 

 

As commentators including The Daily Mail pointed out, Meghan paid tribute to Diana through her clothing as well, wearing a denim button-up shirt and jeans that were strikingly similar to a casual double-denim outfit Diana favoured in her post-royal divorce phase. (Meghan also appears to have been wearing her late mother-in-law’s gold Cartier Tank watch a lot recently.) It does seem deliberate, but it could also have been a fortuitous accident given so many of Princess Diana’s style choices still feel exceedingly fresh some two decades plus after she passed away.

Had one person in Antarctica failed to notice that Princess Diana is an enduringly relevant fashion muse, well, Harry Styles took that holdout to school last November. He stepped out in a Lanvin sweater vest populated by sheep, and the internet sprang to point out an almost identical archival shot of a newly wedded Diana in 1981 wearing a red version. Styles even echoed Diana’s shirt-collar pairing, though not her little black bow—or her wink-wink single black sheep. He’s not the only young thing following in her footsteps—Vogue Paris had a little fun last fall dressing up Hailey Bieber in some of Diana’s most iconic casual looks. 

That the princess’s off-duty style has endured so richly is a tribute to what she was best at with fashion: She was witty, she was cheeky, she knew how to project bold confidence even when she didn’t feel it. She loved a good ugly sweater, or jumper as the Brits would say. (The original sheep sweater was by a label now lost to the sands of time: Sally Muir and Joan Osborne.)

 

 
 
 
 
 
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Contrary to Jenner/Hadid title claims, the Princess of Wales was most certainly the one who brought bike shorts to the streets on her morning gym runs, some two full decades prior to their Calabasas resurgence. She also favoured oversized message sweatshirts, boxy jackets, high-waisted khaki shorts, ball caps (for paparazzi shade), prairie dresses, gingham, florals, a great white shirt moment, a one-piece swimsuit and pale blue, high-rise, straight-leg jeans. Oh, and dorky athletic socks. All things we are wearing eagerly right now. The Everlane website is basically a locker-worthy Diana poster from 1995.

That Princess Diana is so inspiring right now is no surprise. The wealth of pre-internet photos we have of her both on-duty and off somehow make sense of the current rehashed mashup of ’80s and ’90s trends. She defined aspirational British country style (tweed and wellies) and the Sloane Ranger frilly preppy looks of the 1980s (polka dots, hat bands and ruffles). Then, as she inched toward her divorce, she brought her fashion along with her on her emancipation: She came to embody the sleeker, more urban-influenced 1990s. A woman freed from ornamental status, ready to make her mark. That is the spirit of Diana that is resonating so vibrantly right now.

princess diana style

See, Diana was a master of sending messages with her clothing. Rendered silent by the palace machine, she was nonetheless able to use the press pack that hounded her as her voice. Yes, she danced with the devil: She was friendly with the press; she flirted with every camera. Those pictures were gold for the photographers who sold them to the tabloids. They were motivated, but she was too: Diana knew that in order to control her narrative she had to control her image. Those off-duty looks were created by and for her alone: They gave us a glimpse at who she really was under the tiara.

But the wealth of Diana-at-leisure shots we love to pillage for style inspo also have an undercurrent of tragedy. Beyond contributing to her death in a car crash—conflicting reports say it was caused by a paparazzi chase or a drunk driver or some lethal combination of the two—Diana was hounded by photographers’ lenses in life. In 1993, unthinkably intrusive shots surfaced of Diana taken from inside her gym. There were hidden cameras in the gym equipment. On this rare occasion, she sued for invasion of privacy.

Thereafter she took playful revenge, walking to and from the gym wearing the same Virgin Atlantic sweatshirt (a gift from Richard Branson himself) and peach bike shorts over and over, so that the photogs were denied a “fresh” shot. Checkmate! Her assistant sold that sweatshirt, which was gifted to her by the princess, last year at auction for some $68,000.

 

 
 
 
 
 
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Diana’s shadow looms so large, but she was actually in the public eye for only 15 years, from her engagement at 19 to her death at 36, in 1997. Yet she is still a prominent part of the public dialogue, 25 years after her death. Diana is in the headlines all the time due to a unique confluence of factors—the general passion for all things royal, our nostalgia for all things ’80s and ’90s, the fairy-tale marriages of her two sons, and the births of her four grandchildren.

Princes William and Harry both evoked their mother on their recent tours—Harry was brought to tears retracing her steps in Angola’s land mine fields. Kate and Meghan often wear outfits or accessories in tribute to their late mother-in-law, whom they never met—for instance, Meghan wore a wide-brimmed black hat and coat to a 2019 Remembrance Day service that recalled a similar Diana look from 1991.

princess diana style

We don’t see Kate and Meghan out and about off-duty in pap shots as much as we did Diana. Partly, they’re more self-protective—you won’t see Meghan strolling to her regular workout; she had a private yoga room built into the Frogmore Cottage reno and no doubt has a similar space in her current Santa Barbara mansion. But also, though the tabloid media has hardly been kind to Meghan, the push to reduce paparazzi intrusiveness—especially on underaged royal children—after Diana’s death has had some lingering positive effect. 

Until recently, we almost exclusively saw today’s crop of working royals at official events, carefully dressed and coiffed. But during COVID lockdown, Kate and William have mostly been pictured on Zoom calls in more relaxed sweaters and dresses, and since stepping back, Meghan and Harry usually appear in Instagram posts visiting local charities in L.A. like the outing this week—wearing looks that are much less formal but still considered. It’s more relatable, more similar to the way Diana so often was on the daily school run, or the trip to the theme park or the walk to the gym. You can easily imagine yourself in Diana’s belted jeans or oversized T-shirts, much more so than Kate’s glove-fitted coat dresses. So maybe that’s why we all love to look back to the People’s Princess—she gives us the kind of inspiration we can bring to our everyday lives.

 

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