No One Did Denim Better Than Princess Diana

Give me the leisure clothes of a famous woman, and I’ll peer into her soul. How the rich and fabulous choose to let their hair down—no tell-all memoir will ever be as candid.

The Kardashians slink around in spandex and swimsuits that, like their bodies, seem to suspend the laws of nature. Paris Hilton commandeered both a brand (Juicy Couture) and a silhouette (the velour tracksuit) to tell us that she’d never met a label she didn’t love. (Also, that she didn’t mind if it took people that extra second to read the words spelled out on her butt.) But no one dressed down like Princess Diana.

Mandatory Credit: Photo by BRENDAN BEIRNE/Shutterstock (135830b)Princess Diana AND RONALD FERGUSONBritish Royalty at Polo Match, Smiths Lawn, Windsor, Britain  - Jun 1987

British Royalty at Polo Match, Smiths Lawn, Windsor, Britain - Jun 1987

Mandatory Credit: Photo by BRENDAN BEIRNE/Shutterstock (135830b)Princess Diana AND RONALD FERGUSONBritish Royalty at Polo Match, Smiths Lawn, Windsor, Britain - Jun 1987
BRENDAN BEIRNE/Shutterstock

Those of us who spend time in fashion-obsessed corners of the Internet have come across the pre-Internet icon, who, in a darkish turn, gained a fresh fandom after her death: There she is, in bike shorts; oversized sweatshirts; the thick, white socks that creep up her calves; plus sneakers so iconically hideous not even Balenciaga can ever fully reincarnate them. Her activewear could be closer-read than a Wallace Stevens poem. (What do those socks mean? Is ribbed cotton a metaphor for the human condition?) But it’s her denim that has enthralled me. No model off duty could ever.

Mandatory Credit: Photo by CLIVE POSTHLEWAITE/Shutterstock (185830a)PRINCESS DIANA AT HIGHGROVE, GLOUCESTERSHIRE

PRINCESS DIANA AT HIGHGROVE, GLOUCESTERSHIRE

Mandatory Credit: Photo by CLIVE POSTHLEWAITE/Shutterstock (185830a)PRINCESS DIANA AT HIGHGROVE, GLOUCESTERSHIRE
CLIVE POSTHLEWAITE/Shutterstock

From the streets of London to school drop-off to matters of international statesmanship, Princess Di embraced one stu-freakin’-pendous look: a loose top, some ill-fitted pale jeans, and a belt (most of the time.) The effect is pure Diana—instantaneous, telegenic warmth. Think Natasha Richardson in The Parent Trap, Farrah Fawcett on her skateboard, my mother in 1988! These are women to befriend.

Diana, Princess Of Wales, With Prince William At Wetherby School, After Dropping Of Prince Harry. (Photo by Julian Parker/UK Press via Getty Images)

Princess Diana And Prince William Sighting - London

Diana, Princess Of Wales, With Prince William At Wetherby School, After Dropping Of Prince Harry. (Photo by Julian Parker/UK Press via Getty Images)
Julian Parker

I have felt close to Diana in denim since high school but can’t trace, even now, how the fixation developed. (These were the '00s, so Tumblr might have been involved.) All I know is that I was raised by a pair of Diana stans (my parents) who still drink out of commemorative mugs with her face on them. Surely I came across the gowns first; Diana in little black dresses or (ludicrous) sequin sheaths. In those, she looks gorgeous and a little uncomfortable. (Sequins! Itchy.) But at some point, somewhere, I found Diana in denim, and there, Diana at ease.

Mandatory Credit: Photo by Mike Hollist/Daily Mail/Shutterstock (1159338a)Princess Diana And Major Ronald FergusonDiana Princess Of Wales (dead 8/1997) (alone) May 1992. Diana And Major Ron Ferguson At Smith's Lawn.

I liked one photo of her in jeans so much, I taped it into a series of lockers. It’s a paparazzo shot, and the picture of insouciance. In it, her head is tilted as if she’s been forced to interact with her dottiest old British relatives. She wears a flat-brimmed baseball hat, a white crewneck sweater embroidered with a giant red balloon, a blazer in which at least three Dianas could have fit, and a pair of peg-legged blue jeans.

WINDSOR, UNITED KINGDOM - MAY 02:  Diana, Princess Of Wales At Guards Polo Club.  The Princess Is Casually Dressed In A Sweatshirt With The British Lung Foundation Logo On The Front, Jeans, Boots And A Baseball Cap.  (Photo by Tim Graham/Getty Images)

The upshot is equal parts Steve Urkel and Diane Keaton; squint, and Lisa Vanderpump is almost visible. Her expression, her outfit—it doesn’t quite spell IDGAF, and she isn’t “pulling off” some trend (mom-ish jeans are not a pair of micro sunglasses.) Her point is subtler: I’m in control. She looks like she runs shit. What more did I dream of at 15 than that ease?

Mandatory Credit: Photo by Alex Lentati/Evening Standard/Shutterstock (1132924a)Princess DianaA Smiling Diana Princess Of Wales Pictured After Dropping Prince Harry Off At School She Is Wearing Cowboy Boots And A Baseball Cap.

Later, once Kate Middleton and then Meghan Markle arrived on the scene, an endless stream of nostalgia-bait slideshows—which, to be clear, I love—introduced me to even more of Diana’s denim numbers. Aminatou Sow, who cohosts the superlative Call Your Girlfriend podcast, started to chronicle Diana’s lesser-known outfits on Instagram like it was a moral imperative. (Thank you, Amina.) I tapped past denim plus a white shirt and tan belt, denim plus a black crewneck and loafers, denim in the form of one questionable pair of overalls…. Sometimes Amina shared Diana’s black-tie looks, occasions on which she forwent the denim. Still, a strain of wackiness remained. The woman wore mismatched opera gloves. She pinned flowers in her hair. She wore insane bolero jackets. I devoured it all.

No matter the outfit particulars, the end result was the same. There was Diana, looking like a cuddlier Tilda Swinton. Queen, rebel, platonic ideal.

Mandatory Credit: Photo by Keith Waldegrave/Mail On Sunday/Shutterstock (960621a)Princess Diana In Bosnia Where She Was Continuing To Promote The Red Cross Landmines Campaign.Diana Princess Of Wales In Bosnia Where She Was Continuing To Promote The Red Cross Landmines Campaign.

For at least decade, I was content just to admire. Like Madonna or Iman, Diana oozed an unreplicable cool, and I didn’t dare attempt to emulate it. But now I’m 26, it’s 2018, and Diana denim has never been more on trend.

Somehow I’ve amassed a collection of giant blazers and sweaters. I wear baseball hats (to baseball games). I inherited most of my grandmother’s expensive leather belts, the kind with the buckles that make all outfits look regal. I had all the pieces; I just needed the jeans.

Mandatory Credit: Photo by David Hartley/Shutterstock (198706a)PRINCESS DIANA AND PRINCE WILLIAMPRINCESS DIANA AND PRINCE WILLIAM SHOPPING IN CIRENCESTER, BRITAIN - 1992

PRINCESS DIANA AND PRINCE WILLIAM SHOPPING IN CIRENCESTER, BRITAIN - 1992

Mandatory Credit: Photo by David Hartley/Shutterstock (198706a)PRINCESS DIANA AND PRINCE WILLIAMPRINCESS DIANA AND PRINCE WILLIAM SHOPPING IN CIRENCESTER, BRITAIN - 1992
David Hartley/Shutterstock

Earlier this summer I set out to find a pair, à la Di. Eleven bazillion tries later, I found winners at Topshop (MOTO Mid Blue Step Hem), ALEXACHUNG (Mid-Rise Straight Leg), and the one that I ended up with: the Cousin Fit in Isla from NEED. They’re not quite as jolie laide as Diana’s, but I feel they’d do her proud.

Paul Burrell (left, in the background in the white shirt and black trousers, butler to Diana, Princess of Wales as she makes a three day visit to Bosnia - Herzegovina as part of her campaign to raise awareness about the devastating effects landmines have on peoples lives and to call for a complete ban on the production, sale and use of land mines. The trip was organised by the American-based Landmine Survivors Network. Picture taken 10th August 1997. (Photo by Kent Gavin/Mirrorpix/Getty Images)

For the record, when it comes to Diana ‘fits, I don’t have favorites, but I must admit I do like to come back to a shot of Diana in one of her lightest pairs of jeans, with an even higher waist than usual. In the photo she’s in Angola on a Red Cross mission. In addition to the jeans, she wears a belt, a pale turquoise oxford, a double-breasted jacket that gives off Balmain-laced fumes, and a pair of Supergas.

Mandatory Credit: Photo by Tim Rooke/Shutterstock (268567ch)Princess DianaPrincess Diana's visit to Angola - 1997

Princess Diana's visit to Angola - 1997

Mandatory Credit: Photo by Tim Rooke/Shutterstock (268567ch)Princess DianaPrincess Diana's visit to Angola - 1997
Tim Rooke/Shutterstock

To some extent, all the proportions are out of whack—the blazer doesn’t fit, for starters; the jeans should at least nip in at the bottom. And aren’t sneakers a diplomatic faux pas? But the combination is, to be frank, perfection. Just right. The ne plus ultra. It makes me (1) want to be a better person. And (2) wonder…do I need another pair of jeans?

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