We're Obsessed With Carolyn Bessette-Kennedy's Iconic Style All Over Again

359625 01 mags please call john f kennedy, jr editor of george magazine, gives his wife carolyn a kiss on the cheek during the annual white house correspondents dinner may 1, 1999 in washington, dc july 16, 2000 marks the one year anniversary of the plane crash which killed kennedy, his wife and sister in law photo by tyler malloryliaison
Carolyn Bessette-Kennedy Will Always Be In StyleTyler Mallory - Getty Images

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, 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

carolyn bessette kennedy style
Carolyn Bessette-Kennedy in 1996.Lawrence Schwartzwald - Getty Images

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.

Effortless Eveningwear

carolyn bessette kennedy style
Carolyn Bessette-Kennedy at a museum gala in 1999.Evan Agostini - Getty Images

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.

The Pencil Skirt

united states october 06 john f kennedy jr and bride carolyn bessette kennedy stand in front of their apartment in tribecca photo by jon nasony daily news archive via getty images
Carolyn Bessette-Kennedy and JFK Jr. in 1996.New York Daily News Archive - Getty Images

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.

All Black And Off-The-Shoulder

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.

The Camel Coat

carolyn bessette kennedy style
Carolyn Bessette-Kennedy walks her dog with John F. Kennedy Junior in 1998.Lawrence Schwartzwald - Getty Images

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.

White At Night

carolyn bessette kennedy attends the ninth annual fire ice ball, benefitting the revlonucla womens cancer research program, at universal studios in los angeles, california, on december 9, 1998 photo by donato sardellapenske media via getty images
Carolyn Bessette-Kennedy at the Fire and Ice ball in 1998.Penske Media - Getty Images

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 Smart Black Coat

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.


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