Carolyn Bessette-Kennedy’s Nineties Style

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, $520The Leather Knee-High Boot: Loeffler Randall Jaden pointed toe heels, $395The Signature Bag: Prada Sfumato Galleria top-handle bag, $4,700The Power Headband: Mango tortoiseshell-effect headband, $26The Tailored Blazer: Cos slim collarless single-breasted blazer, $135The Strapless LBD: Matteau strapless wool-blend cape maxi, $600The Red Lip: Chanel Rouge Allure Luminous Intense lip color, $48Getty Images

Dressed-Up ShirtingWhen 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.

Acler

Balderstone maxi skirt

Aeyde

Wilma leather sandals

Loewe

Flamenco fringe shoulder bag

Getty Images

Naked SandalsThis 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.

Veronica Beard

Mazzy cashmere turtleneck

Ron Galella

A Form-Fitting LBDEvening 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.

Matteau

strapless maxi dress

Cornelia James

Desdemona opera gloves

Dorsey

Kate Rivière bracelet

Loeffler Randall

Jaden pointed toe heels

Getty Images

The Power HeadbandHair 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.

Mango

tortoiseshell-effect headband

Khaite

x Oliver People 1969C sunglasses

The Frankie Shop

Jude nylon trench coat

Yves Salomon

sheep shearling scarf

Getty Images

The Slinky SlipBias-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.

Issa silk-satin nightdress

J.Crew

New Stevie knee-high boots

Getty Images

Beige and BlackOnce 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.

Theory

flannel midi trouser skirt

Loeffler Randall

Goldy knee-high boots

Éterne

long-sleeve crewneck top

Prada

Sfumato Galleria top-handle bag

Jeff Kravitz

A Slick of Red LipstickBessette-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.

House of Dagmar

collarless wool-blend blazer

Chanel

Rouge Allure Luminous Intense lip color

Hunting Season

Compact satin clutch

Brooks Kraft

A Chiffon DetailA 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.

Manolo Blahnik

Carolyne 70 slingback pumps

Getty Images

The BandanaMuch 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.

Madewell

small silk bandana

Agolde

90s Pinch Waist jeans

Cos

slim collarless single-breasted blazer

Buck Mason

scoop neck tank

Getty Images

The Floral Midi DressBessette-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.

Réalisation

the Monica dress

Stone and Strand

gold diamond ring

Alaïa

Le Teckel leather shoulder bag