In honor of Princess Diana's fashion legacy (which still lives on today!), we rounded up some of the most iconic looks of the People's Princess. We trace her evolution as princess-in-training to full-fledged fashion icon, and recount the stories behind the outfits that catapulted her to the style hall of fame.
The Engagement Look
Long before Kate Middleton wore her iconic blue Issa engagement dress and that sapphire engagement ring; Diana, then 19, showed up on the arm of Prince Charles for their engagement announcement clad in a royal blue skirt suit and pussy bow blouse which matched her ring perfectly.
The Wedding Dress
You know this; your mother knows this. It's the wedding gown that everyone thinks about when someone says "royal wedding." Complete with a 25-foot train and voluminous mutton-leg sleeves, it was the gown on every girl's mind—well, during the '80s, at least.
The Bow Blouse
Diana's feathered hairstyle took on a life of its own, creating copycat looks all over the globe; so when she did something different, it made waves. This ensemble is dubbed the Teddy Boy look, and featured a tweed suit, oversized bow blouse, and pulled-back hair.
The Velvet Gown
When she visited the White House with Prince Charles, Diana turned heads in an off-shoulder midnight blue velvet gown paired with a pearl and sapphire choker. Famously twirling across the ballroom floor with none other than John Travolta, Diana cemented her fashion icon status with this sleek ball gown.
The Majorette Coat
Diana knew how to dress for the occasion—she wore a military-inspired coat by Catherine Walker to a military parade at Sandhurst. The white majorette coat paired with matching hat and all-white accessories made for an iconic look that's striking and timeless.
The Elvis Dress
Famously dubbed the Elvis dress, Diana's pearl-encrusted gown and bolero, designed by Catherine Walker, was actually inspired by Elizabethan ruffs popularized by Queen Elizabeth I. The sleek combination showcased the Cambridge Lover's Knot tiara, one of Diana's most iconic tiaras.
The Grace Kelly Gown
Inspired by Grace Kelly's gown in To Catch a Thief, Diana's ice blue gown with its flowy skirt and matching scarf is equal parts Old Hollywood glamour and regal royal (after all, Grace Kelly was a princess, too!).
The Jackie O. Suit
Grace Kelly wasn't the only fashion icon Diana took inspiration from. In this Versace pink skirt suit and pillbox hat, Diana channeled one of America's most iconic first ladies, Jacqueline Kennedy Onassis.
The Classic Skirt Suit
Here, Diana took inspiration from her mother-in-law's own style. Queen Elizabeth II usually wears a coat dress perfectly matched with a wide brim hat, and Diana nails the look in a white and black combo that is Queen-approved.
The Blazer and Jeans
Diana's off-duty style in the '90s will surely resonate with millennials. For a trip to Eton College to see Prince William, Diana kept it cool and casual in an oversized blazer, loafers, and high-waist jeans.
The Taj Mahal Suit
In a color-block red and purple suit, Diana sat by the Taj Mahal in what has now become an iconic photo. The photo made headlines across the globe as it featured a pensive Diana alone in the world-famous monument to love, signaling the end of her marriage to Prince Charles.
The Floral Gown
In a painted silk floral column gown with a small train, Diana showed off her adventurous side at the premiere of When the Whales Came. A fun print in a classic silhouette made for a look that's elegant yet quirky.
The Red Dress
After her divorce, Diana veered away from conservative looks, and instead favored sleek and tailored dresses that showed off her figure. The new Diana was a confident style star, as evidenced by this bold cinched-waist red dress.
The Blue Dress
No more Shy Di! Diana continued to favor mini dresses in fitted silhouettes, asserting her newfound fashion independence from the knee-length skirts and covered-up pieces that characterized her as the Princess of Wales. In an ice-blue beaded mini dress paired with a diamond and pearl necklace from Garrard, Diana also debuted a shorter, sleeker 'do as part of her new image.
The Ultra-Glam Gown
She couldn't be more different than when she was first presented to the world! In this photo by legendary photographer Patrick Demarchelier, Diana exuded confidence with her slicked-back hair and metallic low-cut gown.
The Versace Dress
You can't go wrong with white, especially when it's by Versace. Along with a Chanel handbag and heels, the former Princess of Wales was ready to take on the world with a style and image that was all her own—a blend of classic and modern that showcased her impeccable fashion sense.
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