Why Carolyn Bessette-Kennedy is the ultimate ‘90s style icon

Fashion’s nostalgia for the 1990s shows no signs of waning, bringing with it a renewed appreciation for the era’s biggest style icons – and none were more prolific 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 splashed across newspapers around the world. 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 editors’ 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. Ports 1961’s AW19 collection took inspiration from her clean lines and subdued colour palettes, Alexander Wang cited her as a beauty muse and Maryam Nassir Zadeh has taken cues from her season after season. To emulate her look, picks seven staples to stock up on now.

Dressed-up shirting
As seen at: Jacquemus

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 shirt into an eveningwear essential (see above), 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, it was the epitome of uptown glamour without compromising on her pared-back aesthetic. For summer soirées, channel the look in a plunging Jacquemus white shirt and Molly Goddard’s ruffled navy skirt. 

SS19’s naked sandals
As seen at: Sonia Rykiel; Rejina Pyo; The Row; ATP Atelier

This season’s must-have shoe was a favourite of Bessette-Kennedy’s: the thin-strapped, minimal mid-heel, as seen on the runway at Sonia Rykiel and Rejina Pyo. For dressier options look to The Row, while commuter-friendly flat iterations can be found at ATP Atelier, Emme Parsons and Ancient Greek Sandals. Worn with cropped jeans and a tank, they spell insouciant ease.

The power headband
As seen at: Prada; Simone Rocha; Alexandre de Paris; Lele Sadoughi

Silk-satin headgear might be back at Prada, but Bessette-Kennedy was an early advocate, regularly pairing a broad tortoise-shell Alice band with oval shades and a white T-shirt. Structured styles abound at Simone Rocha, Alexandre de Paris and Lele Sadoughi, proving that the prim, childhood staple can translate to the streets of New York, the boardroom and beyond.

The slinky slip
As seen at: Paco Rabanne; Alberta Ferretti; Refine

Bias-cut slips formed the backbone of Bessette-Kennedy’s wardrobe, from her Narciso Rodriguez wedding gown to black minidresses worn during blistering summers in the city and ribbed grey styles hidden under cover-ups for cooler days. With a slip dress revival on the catwalk at Paco Rabanne and Alberta Ferretti, new brands are eager to meet the growing demand. Try London-based label Refine, which offers mid-length slips in black, white and dark chocolate, fittingly named “The Carolyn”. For true devotees, there are even headbands to match.

Beige and black
As seen at: Burberry

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. For a fresh-off-the-runway version, look no further than Burberry, where Riccardo Tisci’s debut collection for the house ran the gamut from heritage trenches to coffee-coloured skirt suits. 

The funky bandana
As seen at: Emilia Wickstead; Tom Ford

Much like her mother-in-law Jacqueline Kennedy, who covered her hair with loosely tied silk scarves while holidaying in Capri, Bessette-Kennedy had a penchant for block-colour bandanas. Paired with denim, a tank and a longline blazer, it’s the ultimate in modern Riviera chic. For pretty pastel shades head to Emilia Wickstead, while Tom Ford makes a case for classic black.

The floral midi dress
As seen at: Rouje; Reformation; Réalisation Par

Bessette-Kennedy knew how to turn up the volume on a floaty summer frock: just add stilettos, bed-head hair and a black patent Prada bag for an off-duty look that’s equal parts polished and effortlessly cool. Hunt down the perfect floral midi dress at Rouje, Reformation or Réalisation Par, and combine with shiny accessories that lend a subversive edge.

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