Carolyn Bessette Kennedy’s Best Fashion Moments Ahead of Auction

While we might not know as much of her as we’d like, Carolyn Bessette Kennedy will forever be remembered in American history as the ever-so-stylish wife of JFK Jr. In fact, in addition to making headlines about their relationship, Bessette Kennedy’s style will go down in the books as one of the most elegant and sophisticated celebrity styles ever.
“Long blonde hair, an iconic red lip, and effortless style—all signatures of fashion icon Carolyn Bessette Kennedy,” Sunita Kumar Nair’s book on her style summarized. “Carolyn used fashion as her medium. She hadn’t found her voice yet in front of the camera as Mrs. Kennedy, so she let her fashion speak to the world for her. With her attention to detail, strict color palette, and unique, unidentifiable looks with the brand labels deliberately removed, she was the essence of class—no label would ever define her.”
Right after the release of Ryan Murphy’s Love Story premiered, it seems people can now buy pieces from Carolyn’s wardrobe! Per Vogue, independent auctioneer Lucy Bishop, also known as The Fashion Auctioneer, opened an auction on 25 lots linked to Bessette-Kennedy’s wardrobe (including some staple pieces in this slideshow).
So, in honor of Love Story and the new auction, check out Carolyn Bessette Kennedy’s best fashion looks below!
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Sticking to Classics
Image Credit: Evan Agostini/Liaison
While Bessette Kennedy sometimes dared with some unique outfits, she also looked incredible in closet staples like this classic white button-down and black skirt at the Annual Fundraising Gala in 1999.
Fun fact: This Yohji Yamamoto black silk-wool skirt is one of the pieces going up for auction!
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Layering Up
Image Credit: Mitchell Gerber/Corbis/VCG via Getty Images
Bessette Kennedy wasn’t afraid to layer up during the colder seasons either, including this statement black coat and matching scarf.
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Shoe Magic
Image Credit: Jon Naso/NY Daily News Archive via Getty Images
While her clothes were always ultra sophisticated, her shoe choices, like these brown boots with chunky heels were a major scene stealer.
This Prada camel wool pencil skirt from the Fall-Winter colection is another piece going up for auction!
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Not Afraid of Color
Image Credit: Evan Agostini/Liaison
She also proved she wasn’t afraid of color, even on the colder months, like in this textured red coat.
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Sticking to Neutrals
Image Credit: Lawrence Schwartzwald/Sygma via Getty Images
Bessette Kennedy’s favorite colors were definitely neutrals like black, white, and nude.
And this nude coat, which happens to be a Prada single-breasted coat is also available for auction!
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Going for Unique
Image Credit: Ron Galella/Ron Galella Collection via Getty Images
Bessette Kennedy also dared to wear some unique outfits like this ruffled shirt at 1999’s Newmans Own George Awards.
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Straight Lines
Image Credit: Carmen Valdes/Ron Galella Collection via Getty Images
In this look, the stark off-the-shoulder neckline made her look ultra-elegant and sophisticated.
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All in the Accessories
Image Credit: Jon Naso/NY Daily News Archive via Getty Images
In addition to her impeccable shoes, Bessette Kennedy also wore some statement accessories like this black hairband and circular sunglasses.
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Keeping it Simple
Image Credit: Corbis via Getty Images
When Bessette-Kennedy wore unique pieces like this cream-colored dress to the Fire and Ice Ball, she kept the rest of her look, from her hair to her accessories, quite simple.
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Red Lips
Image Credit: Justin Ide/Newsmakers
To understand Bessette Kennedy’s style, we need to also understand her love for a classic red lips. Always so stunning!
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A Trendsetter
Image Credit: Steve Eichner/Penske Media via Getty Images
Long before wearing gloves on the carpet was a trend, Bessette Kennedy wowed in this strapless dress and long velvet gloves Municipal Art Society’s Grand Central Station re-opening in 1998.
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Casually Chic
Image Credit: Lawrence Schwartzwald
From the headband to the jeans, Bessette knew how to rock something so simplistically chic!
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Bold & Sheer
Image Credit: NY Daily News via Getty Images
This look was so bold for the 90s, but 30 years later, the sheer black dress would become a staple!



