It seems that everyone’s feeling nostalgic about John F. Kennedy Jr. and Carolyn Bessette-Kennedy at the moment, given this year marks the 25th anniversary of their tragic death and the fact that a new TV series about the couple, entitled American Love Story, is currently in the works.
But for many of us in the fashion world, Carolyn Bessette-Kennedy has always been front of mind. I, for one, have had photos of the American socialite on my moodboard for as long as I can remember. Understated yet impeccable, chic but effortlessly so, easy-breezy yet perfectly put-together, fresh-faced and achingly beautiful, Bessette-Kennedy became an unwitting ‘It Girl’ and fashion icon the moment she stepped onto the New York City scene all those decades ago – first as a Calvin Klein publicist, then as JFK Jr.’s partner and later in that Calvin Klein wedding dress as a wife – and has remained the epitome of Nineties minimalist style ever since.
Despite her untimely end – the high-profile couple tragically died in a private plane crash in 1999 – Bessette-Kennedy’s fashion legacy not only endures, but continues to grow stronger. Just put it down to her genuinely timeless elegance, and our ever-increasing nostalgia for the simpler times, and style, pre-influencers, big logos and all-sponsored-everything.
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Here, we take a look back at some of the most iconic looks that best exemplify Carolyn Bessette-Kennedy’s inimitable style – as well as breaking down how to recreate them for the modern day.
Jeans And A White Tee
American classics of blue jeans and a white t-shirt are elevated to the height of casual-chic courtesy of a longline jacket, fur scarf, leather boots and Bessette-Kennedy’s go-to oval sunglasses and preppy tortoiseshell headband.
Veronica Beard Carson Kick-Flare Jean
Le Specs Outta Love Oval Frame Sunglasses
COS Shrunken Slim T-Shirt
Effortless Eveningwear
Carolyn Bessette-Kennedy at a museum gala in 1999.
Few have the ability to make wardrobe ‘basics’ look as elegant as Bessette-Kennedy, who attended a black-tie event in New York wearing a simple white shirt tucked into a black maxi skirt, and still outshone all the other stars in attendance. She kept her accessories typically minimal, too, adding only a pair of black heeled mules and a gold beaded bag.
Manolo Blahnik Callamu 50 Patent-Leather Mules
Norma Kamali Oversized Cotton Bodysuit
Saint Laurent Ruched High-Rise Satin Maxi Skirt
The Pencil Skirt
Carolyn Bessette-Kennedy and JFK Jr. in 1996.
Bessette-Kennedy’s take on minimalist workwear saw her ingeniously combine a beige pencil skirt with dark brown, square-toe heeled boots and a black jumper. Her low ponytail and black shoulder bag completed the pared-back look, that feels very Prada-esque and bang on trend still today.
Miu Miu Leather Knee-High Boots
Theory Maxi Trouser Skirt In Stretch Flannel
Prada Re-Edition 1995 Brushed-Leather Medium Handbag
All Black And Off-The-Shoulder
The Kennedys in 1997.
The Kennedys in 1998.
Bessette-Kennedy’s go-to for glitzy evening events was head-to-toe black and an off-the-shoulder neckline. To attend an event in New York, the late socialite layered a silk slip skirt with a tight, longline top, while for the Municipal Art Society gala she opted for a classic strapless tube dress worn with opera gloves for a bare-shoulder look. Her signature chignon hairstyle and red lip were just the chic cherry on top.
Another Tomorrow Off The Shoulder Jersey Top
Alex Perry Callan Strapless Crepe Midi Dress
Dries Van Noten Long Gloves
The Camel Coat
Carolyn Bessette-Kennedy walks her dog with John F. Kennedy Junior in 1998.
Carolyn Bessette-Kennedy provides all the proof we need that a camel coat is a worthwhile and entirely necessary winter wardrobe investment. We love her belted style paired simply with jeans, leather boots and a large black bag for chilly days in the city.
Mango Belted Manteco Wool Coat
Prada Vintage ’90s Belted Twill Coat
Burberry Wool Cashmere Coat
White At Night
Carolyn Bessette-Kennedy at the Fire and Ice ball in 1998.
As Bessette-Kennedy proved early on, a white dress doesn’t solely suit a walk down the aisle, but can make for an impactful eveningwear look as well. To attend an event in Los Angeles, the socialite exuded an ultra-elegant, First Lady vibe in a high-neck, white tweed gown with a zip down the front, while her loose, undone hairstyle, red lip and strappy sandals added a cool girl element.
The Row Folosa Silk Maxi Dress
Proenza Schouler Joanne Midi Dress
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Acne Studios Efenia Round-Neck Stretch-Woven Maxi Dress
The Smart Black Coat
Carolyn Bessette-Kennedy and JFK Junior in 1996.
The couple in 1997.
Carolyn Bessette-Kennedy knew the power of a black tailored coat all too well. The right one can smarten up even the most laid-back of outfits while also keeping the New York City chill at bay. Here, she styles the outerwear staple just as easily with a dress and knee-high suede boots, as with straight-leg jeans, loafers and a turtleneck jumper. Plus, as ever, her signature headband.
COS Tailored Double-Faced Wool Coat
Mango Tortoiseshell-Effect Headband
Manolo Blahnik Pitana 70 Suede Knee Boots
&Other Stories Single-Breasted Wool Coat
H&M Slim Straight High Ankle Jeans
Aeyde Oscar Leather Loafers
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Clementina Jackson is Acting Site Fashion Editor at ELLE UK, working across news and features, trends, e-commerce and SEO. She was previously Fashion Editor at Cosmopolitan and Women’s Health, and Acting Digital Fashion Editor at ELLE UK, where she was named as a PPA 30 Under 30 award winner for her work on size inclusivity. An experienced fashion, travel and luxury lifestyle journalist, Clementina has also written for Harper’s Bazaar, Vanity Fair, Condé Nast Traveller, Tatler, Red and Italy Segreta.