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Fashion’s nostalgia for the ’90s shows no signs of waning, bringing with it a renewed appreciation for the era’s biggest style icons—and none were more admired than Carolyn Bessette-Kennedy. The impeccably dressed Calvin Klein executive first entered the public eye when she began dating John F. Kennedy Jr. in 1994. Two years later, the pair married on the remote island of Cumberland in Georgia. The bride wore a silk gown by Narciso Rodriguez and beaded Manolo Blahnik sandals, a look that was splashed across newspapers around the world and went on to define Carolyn Bessette-Kennedy’s style. In the years that followed, it was her effortlessly cool street style that stole the show. Fresh-faced and tousled-haired, she became a byword for turn-of-the-century minimalism and established the modern-day fashion editor’s uniform: sleek, understated separates that never go out of style.
Though Bessette-Kennedy’s life has been overshadowed by her tragic death in a plane crash in 1999, her fashion legacy lives on. She has featured on designers’ mood boards for the past two decades, and in recent months the industry’s fascination has only intensified. As a part of its Fashion Icons auction, which begins on November 27th, Sotheby’s has included three of CBK’s iconic coats—including a leopard one. If you’d like to emulate her style a bit sooner, shop the 10 looks in our edit below.
Vogue’s Guide to Carolyn Bessette-Kennedy’s Style:
- The Everyday Denim: Khaite Abigail jeans, $520
- The Leather Knee-High Boot: Loeffler Randall Jaden pointed toe heels, $395
- The Signature Bag: Prada Sfumato Galleria top-handle bag, $4,700
- The Power Headband: Mango tortoiseshell-effect headband, $26
- The Tailored Blazer: Cos slim collarless single-breasted blazer, $135
- The Strapless LBD: Matteau strapless wool-blend cape maxi, $600
- The Red Lip: Chanel Rouge Allure Luminous Intense lip color, $48
Dressed-Up Shirting
When it came to elevating classic pieces, few could compete with Bessette-Kennedy. For a black-tie gala at the Whitney Museum of American Art, she transformed a white button-down into an eveningwear essential, unbuttoning it to the breastbone, rolling up the sleeves and adding a floor-skimming tiered skirt. Accessorised with black sandals and a gold beaded bag, the look was the epitome of uptown glamour without compromising her pared-back aesthetic. For similar semi-formal soirées, channel the look in a relaxed Nili Lotan button up and Acler’s maxi skirt.
Naked Sandals
This must-have shoe was a favourite of Bessette-Kennedy’s. The insouciant ease of a thin-strapped, minimal mid-heel works just as well with denim as it does with a dress. Look to Totême for inspiration.
A Form-Fitting LBD
Evening gowns don’t get more classic than form-fitting black. Bessette-Kennedy wore hers with elbow-length gloves and pointed stilettos to elevate the simple design, yet kept her hair relaxed in a loose chignon. We love this similar style from Matteau.
The Power Headband
Hair accessories have been back–and bigger than ever–for a while, but Bessette-Kennedy was an early advocate of the more minimalist take, regularly pairing a broad tortoiseshell headband with oval shades and a white T-shirt.
The Slinky Slip
Bias-cut slips formed the backbone of Bessette-Kennedy’s wardrobe, from her Narciso Rodriguez wedding gown to black mini dresses worn during blistering summers in the city and ribbed grey styles hidden under cover-ups on cooler days.
Beige and Black
Once dismissed as an unwearable combination, Bessette-Kennedy was a long-time champion of beige and black in all its forms: a pale fawn pencil skirt with a black knit and brown boots; a black T-shirt with camel-hued trousers and loafers; dark caramel cords with a black turtleneck.
A Slick of Red Lipstick
Bessette-Kennedy’s beauty looks were like her outfits: simple, yet effective. When she did amp things up with red lipstick, her preference was a rich hue apparently applied with her ring finger, to achieve a “bled” effect. Follow suit by adding a just-kissed red pout to a sheer base and a slick of mascara.
A Chiffon Detail
A little black dress doesn’t have to be plain. When in search of a stand-out detail, Bessette-Kennedy preferred to play with texture, rather than print–as evidenced by this tulle overlay.
The Bandana
Much like her mother-in-law Jacqueline Kennedy, who often covered her hair with loosely-tied silk scarves while on holiday in Capri, Bessette-Kennedy had a penchant for block-color bandanas. Paired with denim, a tank, and a longline blazer, it’s the ultimate in city-appropriate Riviera chic.
The Floral Midi Dress
Bessette-Kennedy knew how to turn up the volume on a floaty summer frock: just add stilettos, bed-head hair and a black patent bag for off-duty style that’s equal parts polished and effortlessly cool. Hunt down the perfect floral midi dress and combine it with shiny accessories that lend an edge.
