How Princess Diana Wore Every Outfit to the Max

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As I’ve skated through my mid-twenties and drifted closer and closer to 30, Princess Diana—a figure whom I once previously thought of only in passing as a hallmark of my mother’s generation—has come to loom larger in my mind, perhaps because with age comes the knowledge that femininity and being fucked up universally stride together hand in hand.

I forget which bit of media first sparked my interest, but Tina Brown’s The Diana Chronicles got me hooked. (Brown was the founding editor-in-chief of The Daily Beast.) Like many others, I also digested the sordid royal tale via seasons of The Crown and contextualized my education with Kristen Stewart’s Diana interpretation in Spencer.

Why Princess Diana Will Never Die

There are so many elements of the Princess of Wales to parse through, including her compassion, her raw magnetism and the trauma of her upbringing, but reassessing her best fashion moments is a pastime that never gets old. Long before red carpet moments were painstakingly manufactured to shock and awe, Diana’s clothes communicated for her when she was unable to say what she wished, which is why they continue to radiate through time like heat-seeking missiles. Here are her loudest looks.

Given that Diana’s life has been so relentlessly narrativized, I feel that assessing her outfits non-chronologically represents a welcome deviation from the norm. By 1988, Diana was already a handful of years into her marriage to Prince Charles, and the cracks, spurred on by the latter’s ongoing affair with Camilla Parker-Bowles, were beginning to show.

However, at this Women’s International Tennis Association event, Diana was immaculate, despite her emotional turmoil: this petite, court-ready minidress and cardigan look directly anticipated the post-pandemic tennis girl trend that would sweep New York City more than three decades later.

Everyone talks about the racy black dress Baby Diana wore to her first official royal engagement with her fiancé, but I'm much more partial to the red, sparkly prom-like number she wore to the premiere of For Your Eyes Only one month before her wedding in 1981: it was much more befitting of her age, enthusiasm and the promise her life held at the time.

Let’s skip to the end: Diana died on Aug. 31, 1997, as a result of the injuries she sustained in a Paris car crash, but only weeks earlier, she was posted up in St. Tropez, looking fabulous in the perfect summer cover up: modern slashes of lime green and purple cinch at the waist, matching her one-piece. I hope she’s still chilling on a yacht somewhere in the afterlife.

In addition to her aristocratic good looks and the radiating evidence of a rich inner life, Diana was blessed with another coveted beauty queen quality: she was tall as hell, clocking in at a very respectable 5’ 10”. Just imagine a pipsqueak like Kim Kardashian (5’ 2”) attempting to pull off the statuesque, powder-blue tulle Catherine Walker gown Diana wore to Cannes in 1987, and you’ll gain a new level of respect for the soft authority the princess not just telegraphed, but embodied.

Diana’s height also came in handy when she veered into menswear-inspired looks, like the pure white Jasper Conran skirt suit she selected in 1985. You can look at a million pictures of this woman and still not be able to get over how well she photographed, especially next to a flop like Charles.

Just a year after grinning at the Bond film premiere, Diana was now pregnant and married to the king-to-be at the age of 20, and this opulent red pregnancy gown, created by the couturier David Sassoon, telegraphs the girlish romanticism that must have dominated her fantasies of family life at the time, even as she battled persistent inner demons. Rarely has an actual princess looked so much like a princess.

It’s 1994, and fairy tales are but distant memories. Charles has just confessed to cheating on Diana on national television, but the show must go on, and there’s an event to attend. Diana, undaunted, shows up to a Vanity Fair party that same night wearing what was dubbed the “revenge dress:” an 0ff-the-shoulder black silk cocktail number by Christina Stambolian that stunned the world.

This, unequivocally, is my favorite Diana look of all time. It predicted so much: freak streetwear, hyper-specific shoes, unexpected accessory branding, billowy silhouettes in counterintuitive ensembles. Diana is wearing a white sweatshirt and white sweatpants tucked into brown leopard-print cowboy boots, and she’s topped the whole thing off with a tailored gray blazer and tucked her hair into a blue baseball cap decorated with a crown. Her fists are clenched because the genius of this fit is making her nervous.

Diana had a way of adopting the fashions favored by other countries without causing any offense; she was respectfully paying homage to her hosts everywhere she went. The princess wore traditional Pakistani garb on her visits to the country and for liaisons with her friend, Jemima Khan (wife of cricket hero and later Prime Minister Imran Khan).

Catherine Walker was a favorite couturier of Diana’s, and for good reason: the designer had a knack for sheathing the princess’s willowy limbs in garments that never over-sexualized her, but rather perfectly straddled the line between overt femininity and corporatized respectability. This immaculate 1988 suit is a great example: there’s a Hillary Clinton-like polish to the ensemble, but Diana’s earthiness makes it sweet and whimsical.

In addition to weird streetwear, Diana also invented athleisure. The poor woman was so bored and hemmed in by palace restrictions, often, the only jolt she could get out of her day came from the spray of paparazzi photographing her gym excursions. So Diana rose to the occasion, and threw Ivy League sweatshirts over tiny bike shorts and dictated what 21st-century hot girls would wear to sweat henceforth.

It’s a fashion prompt that would catapult many self-professed do-gooders into scandal territory: what do you wear for a photo-op in an Angola minefield? In 1997, Diana kept it simple: white shirt, tan slacks, loafers. Every Instagram humanitarian from here to Tokyo continues to take notes to this day.

What does a royal mom wear to pick up her kids from school? Most royal moms wouldn’t even bother to do it themselves, but Diana rocked the receiving line in a Philadelphia Eagles jacket, of all things. Where did she even get it? Who cares?

Bruce Oldfield, like Catherine Walker, was another Diana standby, and this shimmering silver 1985 gown she chose for a red carpet brilliantly communicates why. Though the look includes subtle shoulder-padding and long sleeves, you could envision Chloë Sevigny putting her own twist on it today. It’s a garment built for It Girls only.

You could write a 50-page senior thesis paper on Diana’s statement sweaters, and I hope someone has. But this iconic Black Sheep jumper, which she wore to a polo match in 1980 while rumors were beginning to swirl about who Charles would elect to marry, arguably dictated the rest of her life in the public eye. While she appeared to blend into the world she grew up in, she was nothing like her peers and nothing like her husband. This subterfuge made her eternally unforgettable.

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