How to Replicate Carolyn Bessette-Kennedy’s Signature Style

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Carolyn Bessette-Kennedy ranks high on our (long) list of historical figures with impeccable fashion taste. While many recognize Bessett-Kennedy for being JFK Jr.’s wife, those in the fashion realm regard the late publicist, first and foremost, as a style icon. One could attribute the accolade to her time as a Calvin Klein executive, though we’d argue that such effortless polish was a natural quality she possessed.

In an exclusive interview with InStyle, fashion stylist and style expert Naina Singla explains that Bessette-Kennedy’s style revolved around three pillars: minimalism, refinement, and sophistication. “Besette-Kennedy had a versatile collection of basics and cherished pieces,” Singla says. “She adhered to her signature timeless style rather than adopting the latest fashion trends and valued wearing structured silhouettes that worked for her body. She dressed for herself and did what made her happy.”

What made Bessette-Kennedy’s style so classic was her focus on basics and a neutral color palette. Luckily for us, her timeless elegance is easy to replicate—here's how.

A Black Top for Every Occasion

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What’s black and white all over? Bessette-Kennedy’s everyday shirt rotation. Judging by the paparazzi photos, the '90s icon had a collection of black tops suitable for every occasion you could imagine. Long sleeves, short sleeves, sleeveless, v-neck, crewneck, turtleneck—she had at least one of each.

A Slip Dress

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“Slip dresses were one of Bessette-Kennedy's favorite go-to pieces,” Singla tells InStyle via email, “and the 90's minimalist trend is popular right now.”

Related: The 19 Best Slip Dresses to Keep in Your Wardrobe Year-Round

A Tailored, White Button-Down

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A crisp white button-down is a staple in capsule wardrobes, especially that of Bessette-Kennedy. She’d pair a tailored fit with trousers or jeans or a midi-length skirt for day wear. Still, one of Bessette-Kennedy’s many styling talents was her knack for elevating basics in such a way that something simple and generally worn for everyday wear into formal attire. The white button-down was no exception. On the night of the 1999 "Brite Nite Whitney" fundraising gala at the Whitney Museum of American Art, for example, she masterfully tucked the top into a black, floor-grazing skirt, accessorizing with sandals and a gold clutch.

Layering Pieces

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Specifically, outerwear. From trench coats to wool coats, bombers, and suit jackets, Bessette-Kennedy consistently completed an outfit with the perfect piece of outerwear. She preferred maxi styles, according to Singla, and loved a belt detail.

A Headpiece

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Blair Waldorf and Lauren Conrad made headpieces cool again in the 2010s, but Bessette-Kennedy was a headband and bandana stan back in the late '80s/'90s (on days when she wasn’t rocking a pony or slightly mussed strands). She’d also reach for a beanie during the winter months.

A Black Dress

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Similar to Bessette-Kennedy’s fixation with black tops, the fashion icon also couldn’t resist a little black dress. There are countless photographs documenting the many LBD stylings of Bessette-Kennedy, from a ruffled number to a sleek, square-neck midi, a cami strapped frock, and a strapless body-hugging moment paired with black velvet opera gloves (to name a few). If the invite said formal attire, she was likely opting for something along these lines.

Interesting Necklines

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Bassette-Kennedy may have stuck to a neutral color palette across her wardrobe, but one of the subtle ways she switched up her look was through different necklines. V-necks, crewnecks, and boatnecks—she tried them all, and it added an element of depth to her looks.

Blue Jeans

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What got between Bessette-Kennedy and her denim? Nothing. Bootcut, flares, straight-leg pairs—she donned them all. Which should come as no surprise. She did work for Calvin Klein, after all.

Related: The 19 Best Jeans for Women That Are Actually Worth Buying

Modest Dressing

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Her father-in-law may have been a democratic leader, but Bassette-Kennedy was a conservative dresser. Whoever said that modest dressing wasn’t chic was sorely mistaken, as this fashion icon proved again and again that you can cover up and still make a statement.

A Good Overcoat

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Like shoes, statement outerwear can transform an outfit from a look that’s simple to an ensemble that stands out. Bassette-Kennedy had a selection of coats and jackets to choose from when the forecast called for extra layers, but she especially loved a maxi style she could relax into.

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