One of the most alluring people in modern history, Diana, Princess of Wales, is an unflagging fashion icon. Since she became royalty in 1981, the enigmatic Princess Diana’s style and daring fashion sense became the blueprint for modern trends.
Princess Diana’s style earned her the nickname “Dynasty Di,” as she loved glitzy, opulent looks. However, her outfits could also be casual enough to align with another one of her nicknames, “The People’s Princess.”
Her ability to be ordinary yet enchanting, flamboyant yet approachable, defines her captivating style.
The Sporty Princess
As the weather cools down this Fall, the Soccer Mom Aesthetic will take over for the Tenniscore we saw all Summer 2024. The Soccer Mom Aesthetic is sporty and ever-so-casual, something Princess Diana practically invented as a fashion statement.
Diana was an active woman, so while this aesthetic was stylishly quirky, it wasn’t just for show. She worked out at a gym, took long power walks, went rollerblading, and did a variety of other exercises.
These hyper-casual outfits did not look traditional for a royal, but Diana broke the mold by being authentically herself.
Active in Spandex
Her gym day chic looks were effortlessly cool and felt youthful and authentic. She wore spandex shorts or, as I like to call them, biker shorts. These shorts were popular in the ‘80s and ‘90s but fell out of fashion for a few decades, coming back in the 2020s.
Diana seemed to have a pair in every color — neon orange, ink black, midnight blue, milk white, eggplant purple, hibiscus pink, crimson red, and so on. She sported these with oversized sweatshirts or long-sleeve tees, creating that big-on-top-little-on-bottom vibe that is popular today.
The Dad Shoe
Along with stretchy shorts and baggy pullovers, Diana wore chunky sneakers and thick crew socks. By the 2000s, most sneakers resembled socks more than shoes. But Princess Diana’s sneaker choice has come back into fashion, and the “Dad shoe” reigns supreme in street style right now.
Models like the New Balance 2002R, New Balance 990v4, Nike Air Monarch IV Training Shoes, Fila Disruptor Shoes, and Skechers Energy Afterburn are great examples. Previously considered ugly, “Dad shoes” can now be elegant and trendy.
Catalog-Worthy Casual
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Image Credit: WikiCommons//Rick, CC BY 2.0.
Countless Princess Di outfits could be cut straight from J. Crew, Land’s End, Burberry, and Vineyard Vines catalogs. They were preppy but also chic and relaxed in many instances.
These looks were a large part of what makes her a fashion icon to this day — they’re timeless and walk the line between laidback and luxurious, which many of us aspire to attain.
She created enviably cool outfits with chunky leather belts, flowy ankle-length skirts, faded blue jeans, loafers, fitted turtlenecks, pleated pants, light button-downs, and bright white sneakers. She managed to look relaxed without looking frumpy or messy, and even when she was a little messy, it felt organically beautiful.
Sailboat and Saddle Chic
These casual and mildly preppy looks were much more fitting for a royal than her laidback gym day looks.
However, her sportiness still came out in these styles. Her outfits often felt influenced by boating, horseback riding, golfing, tennis, and even safariing. Cable-knit, V-neck sweaters, tall leather dining boots, beige boat shoes, baseball caps, Hunter rain boots, and navy blue blazers all embodied royal preppy perfectly.
Simply Elegant Swimwear
Diana loved a good swim, and there are plenty of photos of her having fun on vacation, sunning herself on a boat, or finding a moment of solitude on the water.
She mostly wore simple one-piece silhouettes with thick straps and moderately low-scoop backs. They were modest and lovely. There are photos of her in cheetah print, neon ombre, color-blocked black and white, and all-black suits.
But, thanks to an infamously solemn picture of her dangling her feet off a yacht platform, her aqua-blue bathing suit might be the most well-known. The suit was close to a Tiffany blue, complementing her tan skin and gold-blonde hair. It was so basic but so memorable.
Redefining Denim in Mom Jeans
Diana wore plenty of jeans, which wasn’t typical of female royals but also wasn’t super taboo or anything.
She wore capris, black tailored jeans, and white slim-cut denim. But the faded blue, loose-fitting, high-rise jeans are my favorite, and they paved the way for today’s “Mom jeans” trends. Diana made parent clothes fashionable, from the Dad shoe to the Mom jeans.
Final Touches
As mentioned, Diana loved a chunky belt, black or brown, flat or braided. She wore them with her jeans, pants, dresses, suits, long skirts, and short skirts. They were a small detail that polished every look and flattered her figure.
The princess was known to wear very unique hats, adding to her lavish aura. Think of the fabulous hats we see every year at the Kentucky Derby; her hats were vibrant and elegant but also daring.
Since the paparazzi endlessly harassed her, Princess Di often wore sunglasses when out and about. She was partial to smaller, rounded, or rectangular shades. They were typically very dark in color and sometimes had tortoise shell frames.
However, Diana’s collection of sunglasses was plentiful, and she also wore classic Raybans, dainty horn-rimmed sunglasses, larger ombre glasses, and even sharp straight-browed shades.
The Royal Black Sheep
It’s no secret that Diana didn’t always fit well with the royal family. The pressure to behave, look, and feel a certain way about everything put a lot of pressure on her. It’s easy to paint the royals as villains in this narrative, which Hollywood often does, but Diana’s relationship with them is far more intricate and elusive.
Anyway, we can still call her a black sheep in that gang. Luckily, black looked fabulous on her. Black ballgowns, slinky black evening gowns, suits, little black dresses, sheer tights, and chic handbags are a few ways Diana would go back to black. This color gave Diana an edge that the royal-approved pastels never did.
To me, it was the dresses where she truly shined in black. Shimmery A-line gowns, tea-length velvet dresses with padded shoulders, ruffled strapless gowns, and tailored mid-thigh pencil dresses with showy hats are standouts. However, there is one black look that is part of fashion history.
The Revenge Dress
The Revenge Dress, of course, is one of Diana’s most iconic looks. Christina Stambolian designed this dress for Diana, and she wore it the evening after her husband confessed to his affair. Revenge is supposed to be served cold, but she was hot as hell in this dress.
It broke every rule in the royal book. It was skin-tight, dark black, off-the-shoulder, above her knees, and had a plunging neckline. It was way too sexy for a princess, according to the royals.
She styled the look with skinny, round-toed high heels, extra-sheer black stockings, and a simple square clutch. She wore a dainty jewelry set with teardrop earrings, a bracelet, and a few rings. But the gorgeous pearl and sapphire choker is what dazzles along with the dress.
Queen Mary’s Sapphire
The sapphire in the center once belonged to Queen Mary; Diana received it as a wedding gift from the Queen as tradition. It was a brooch, but Diana had it adorned into a necklace with seven pearls, creating the decadent statement piece for this legendary look.
A Rebel in Pastel
While there is no denying that Diana looked fabulous in black, her many pastel outfits are also a wonderful source of aesthetic inspiration. These may not have the wow factor of her rich black outfits, but they’re refreshing, sweet, and mostly approved by the royals.
Cotton candy-colored evening gowns were ethereal and endearing. Strapless, Grecian powder blue dresses, ballerina pink tulle gowns, and azalea pink frilly dresses gave her an airy aura. Ballerina pink scalloped shift dresses, coral pink skirt suits, and sunny yellow printed midi dresses were some of her best pastel daytime looks.
While these were more royally appropriate, she still made these looks her own, with her flair for elegant accessorizing and inherent magnetism.
The G.O.A.T. of Statement Coats
Diana was the Princess of Statement Coats. Her outerwear collection was unmatched, with jackets and coats in a variety of silhouettes and aesthetics, all of which demanded attention.
An oversized beige winter coat lined with chocolate brown fur, a classic tan peacoat, a cherry red wool coat, an amethyst purple baby-doll coat, and a candy red puffer jacket are stellar examples of her extraordinary outerwear.
Others include a fluffy collared white fur jacket, a watermelon pink ruffled overcoat, a black wool caped coat, and an Eagles letterman jacket.
She was a master of layered looks with these unique and striking coats. Her coat collection ranged from sporty to swanky.
Women’s pantsuits were trendy at the time, but not so much in the royal family. Nevertheless, Diana rocked voguish suits often. Pastel skirt suits were very princessy; think Kate Middleton’s style. But she also wore dark grey double-breasted pantsuits, perfectly tailored camel-colored pantsuits, sailor-style blazers, and even tuxedos!
Princess Diana’s Style: An Enduring Icon in Every Era
From chunky sneakers and stretchy shorts to slender skirt suits and pearl necklaces, there’s something for everyone to love in Princess Diana’s style, and that’s why her fashion legacy is so enduring.
Fashion is aggressively cyclical — from spiky stilettos to chunky block heels, from low-rise jeans to high-waisted denim — but no matter where we are in the cycle, Diana’s fashion taste feels flawless.
“Dynasty Di” wore Dior, Chanel, Jimmy Choo, Versace; yet, her vibe always embodied “The People’s Princess.” Her looks were stunning but felt accessible, and still do, giving us all the chance to emulate her uncomplicated and immaculate sense of style.
