In Honor of Princess Diana's Birthday, We're Looking Back at Some of Her Most Memorable Style Moments

Princess Diana redefined the royal dress code. From her high-fashion wardrobe to her willingness to take sartorial risks (shorter hemlines, lower necklines … the list goes on), she quickly became a style icon. To celebrate the late Princess of Wales’s 57th birthday on Sunday, July 1, we’re looking back at some of our favorite Princess Di outfits.


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Catherine Kast, Style Editor: Diana’s Philip Somerville topper (worn to a visit to the Gulf States in 1989) is utterly perfect with her cobalt-and-white Catherine Walker suit and clutch. Each element of the outfit could be worn individually today, minus perhaps the turban hat, even though I have this feeling Solange would look amazing in it. There are so few occasions these days that merit an ultra-fancy turban hat. But seriously! I can imagine Jenna Dewan-Tatum in the bold pencil skirt with a boxy white crop top, and I strongly believe Elizabeth Banks would look fantastic in that blazer layered over a tailored jumpsuit. Also, Jamie Chung would for sure carry that clutch. Right?


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Brittany Talarico, Style News Editor: You probably forgot that Princess Diana attended the 1996 Met Gala. She wore a navy silk slip dress with black lace detailing from John Galliano’s debut couture collection as the Creative Director of Dior, and completed the boudoir-inspired design with a matching silk robe-like topper and her famous pearl-and-sapphire choker necklace. The Princess of Wales experimented with sexier silhouettes and hemlines in the ’90s and wasn’t afraid to push the fashion envelope, which is one of the reasons I love this look so much.


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Alex Apatoff, Senior Style Editor: This Catherine Walker dress, which Diana dubbed her “Elvis dress,” was such an iconic look on the late princess that it eventually graced her Franklin Mint doll. It then went on display at the Victoria & Albert museum in an exhibit dedicated to British glamour. With more than 20,000 pearls studding the gown and jacket, and especially when worn with a striking tiara (as she did for a state visit to Hong Kong in 1989), this dress is royally elegant, just like Diana herself.


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Andrea Lavinthal, Style and Beauty Director: Princess Di was doing the red dress, red shoes look way before Reese, Blake and Gigi. In 1995 (post-separation from Charles), she stepped out in a head-turning crimson Christian Lacroix dress, paired with coordinating accessories (including red nails!) in Paris.

RELATED PHOTOS: Diana’s Style: From Shy to Chic


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Sarah Kinonen, Style & Beauty Editorial Assistant: While I love almost all of Princess Diana’s elegant gowns and ensembles from the ’80s, her most memorable look, for me, at least, is a trend she didn’t don too often: menswear. Sure the gowns are gorgeous, but this “Teddy Boy” suit (as described by the Internet) is my ultimate favorite. From the gray tweed jacket to its matching skirt with black button detailing, it shows off a different aspect of her style the world never really got to see — and something I wish we would have seem more of.


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Colleen Kratofil, Style Writer-Reporter: Just like Princess Kate today, Princess Diana did casual polo-watching outfits better than anyone else (sorry, polka dot dress from Pretty Woman). She made a mom-tastic print sweatshirt and jeans look incredibly chic with an oversize blazer. And even her equally casual cap is a fun accessory that pulls together her laid-back look. Though the cowboy boots at a polo match are a little puzzling, I think it still works thanks to the whole “riding jacket vibe.”


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Lindsay Schallon, Senior Style Editor: Even in the ’80s trend du jour — crushed velvet — Princess Diana looks regal and radiant. (The photo is from a London premiere in 1985, FYI.) But what has to be the best thing about this ruched, bow-bedecked Catherine Walker number (one of the princess’s go-to designers), is the backward pearl necklace that accompanies it. Yes, Jennifer Lawrence wasn’t the first to do it!


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Jackie Fields, Beauty Editor: The date: June 1, 1983. Just 346 days after the birth of Prince William, rumors of baby number two were abound. And while Princess Diana would get pregnant later that year, on this night she would show off her gorgeous figure in a one-shoulder gown. Accessorizing the clingy piece, worn to the London premiere of Octopussy, with a silver envelope clutch and shoes, the royal not only put to rest any rumblings of a pregnancy (for a few months) but it was one of our first opportunities to see how truly glam she could get.
RELATED VIDEO: Met Gala Flashback: Princess Diana’s 1996 Dior Moment

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