How To Recreate Carolyn Bessette-Kennedy’s Best Minimalist Outfits

Her style is still so relevant.

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Carolyn Bessette-Kennedy's Best Fashion Moments
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One could argue that the late Carolyn Bessette-Kennedy was the original queen of minimalism. As you may know, the Calvin Klein executive first entered the limelight in 1994 when she was romantically linked to John F. Kennedy Jr. (they tied the knot two years later). From there on out, the New Yorker earned praise for her effortlessly chic, no-fuss style; her wardrobe was stocked with pared-back pieces, including slip dresses, white button-downs, pencil skirts, and bootcut jeans. It’s no wonder the style set and designers alike still riff on Bessette-Kennedy’s most iconic fashion moments to this day — they’re that timeless.

In her debut book, CBK: Carolyn Bessette Kennedy: A Life in Fashion, which hit shelves last month, author Sunita Kumar Nair examines the socialite’s never-ending influence on the fashion industry. “On social media, John Jr. and Carolyn’s photos are repeatedly used to represent tokens of taste and sophistication; their images sit alongside moody pictures of Hermès bags, vintage Porsches, Braun clocks, and Jean Prouvé chairs for inspiration boards,” an excerpt from the book explains. What’s more, there are Instagram accounts dedicated to highlighting Bessette-Kennedy’s most sought-after ensembles, a popular one being @cbkalifeinfashion. The writer also touches on how Bessette-Kennedy’s streamlined style paved the way for today’s leading luxury labels, such as The Row, Toteme, and Bottega Veneta.

Below, take a better look at six of Bessette-Kennedy’s best outfits from the ‘90s. Trust: These looks will never go out of style.


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Though she didn’t stray too far from her signature neutral color palette, Bessette-Kennedy threw a sartorial curveball every once in a while. For instance, in ‘96, she was out in New York wearing a flirty pink and purple printed dress and bold colorful tights (which have recently re-entered the fashion scene).

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The publicist made even a casual walk with her furry friend a fashionable affair. On one outing, she kept it simple but sleek, donning a black tank, straight-leg jeans, and strappy sandals. Instead of jewelry, Bessette-Kennedy styled the look with a pared-back watch.

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This off-duty look circa ‘96 will arguably go down in history as her most popular street style moment. Sure, her black and white attire was rather simple — but Bessette-Kennedy’s accessories, which consisted of a tortoiseshell headband, oval-shaped frames, and a fuzzy scarf, took the outfit to cool-girl status.

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A month after getting hitched in Georgia, the newlyweds were pictured leaving their Tribeca apartment. Bessette-Kennedy leaned into understated basics, including a black form-fitting long-sleeve top and a beige calf-hitting pencil skirt. Her glossy red square-toe boots undeniably stole the show.


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Bessette-Kennedy knew the power of a coat the struck the perfect balance of vibrant and practical. This red Prada checkered style, for example, was a go-to for the publicist. During her time in the public eye, she was also snapped wearing more luxurious outerwear, like a vintage leopard look and a black fuzzy jacket.


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The style muse proved one should never underestimate the appeal of a classic white button-down. While attending the Whitney Museum of American Art’s annual fundraising gala in ‘99, Bessette-Kennedy paired the wardrobe essential with what appears to be a black body-hugging maxi skirt. Per usual, the socialite opted for strappy pumps and minimal jewelry.

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