4 times Princess Diana and Carolyn Bessette-Kennedy were 90s style twins


King Charles' late ex-wife and John F. Kennedy Jr's spouse were two incredibly well-dressed women, with a similar style ethos


Princess Diana and Carolyn Bessette-Kennedy
Laura Sutcliffe
Laura SutcliffeFashion and Beauty News Editor
February 27, 2026
Share this:

We have been captivated by the new Disney+ drama series, Love Story: John F. Kennedy Jr. & Carolyn BessetteThe nine-part offering shows the love affair between John and Carolyn and a dazzling display of 90s fashion.

Actress Sarah Pidgeon, whose depiction of Carolyn has been hugely praised, also showcases a variety of sleek and timeless styles throughout the programme that are exact replicas of the beauty's aspirational wardrobe.

Sarah Pidgeon stars as Carolyn Bessette and Paul Anthony Kelly plays John F. Kennedy Jr.© Eric Liebowitz/FX
Sarah Pidgeon stars as Carolyn Bessette and Paul Anthony Kelly plays John F. Kennedy Jr. in the new drama
Carolyn's make-up was equally pared-back, centring on a sweep of mascara and bold red lipstick for evening.© Getty Images

Carolyn Bessette-Kennedy was a famously classic dresser

The late PR executive wasn't known for embracing an array of colours, textures or daring fashion trends; she loved basic styles that were beautifully cut. Her colour palette was littered with creams, blacks, browns and the odd white shirt.

Amanda's tall girl muse? "The late Carolyn Bessette-Kennedy was, and still is, the epitome of quiet sophistication and effortless chic."© Getty Images

Carolyn Bessette-Kennedy was a '90s style icon

Whilst watching the show, I felt there were distinctive parallels between her look and the late Princess Diana, who famously opted for a similar style ethos. Diana's love of regal tailoring and classic pieces mirrors Carolyn's outfit choices.

Recommended videoYou may also likeWATCH: Love Story John F. Kennedy Jr. & Carolyn Bessette - the official trailer

The red coat

Media Image© Getty Images

Carolyn wore a red Prada coat in 1997

Both ladies knew the statement power of a red coat, and although their styles are different in texture, they both create an eye-catching look.

Carolyn was spotted walking her dog with John in NYC in 1997, sporting a red Prada coat. She put a casual spin on the style by adding a black beanie hat to keep out the chill.

Media Image© Getty Images

Diana loved to sport red coats of all varieties

A year earlier, in 1996, Diana was pictured in her scarlet, long-line coat as she left the gym at the Harbour Club in Chelsea. Also making the style more relaxed, she draped a large white scarf around her neck.

The off-the-shoulder gown

Carolyn Bessette-Kennedy (1966 - 1999) and John F Kennedy Jr (1960 - 1999) with Caroline Kennedy-Schlossberg and designer Edwin Schlossberg, attend a Municipal Art Society event (in honor of Jacqueline Kennedy Onassis) at Grand Central Station, New York, New York, October 4, 1998© Getty

Carolyn loved wearing shoulder-exposing dresses

In 1997, Carolyn and John stepped out for a night at the gala at the Whitney Museum. All eyes were on her off-the-shoulder black satin creation and fearless red lipstick.

Wearing the black cocktail dress was a last minute change for the Princess of Wales© Tim Graham

Princess Diana wearing her Christina Stambolian 'revenge' dress in 1994

Jeans and loafers

A simple shirt with denim was a great look for Diana© Getty Images

Diana wore this sleek style combination in 1997

Cropped trousers paired with no socks represent the quintessential Italian aesthetic - a masterclass in effortless sophistication. Diana regularly wore this tried-and-tested formula during the 90s with cropped jeans and a shirt.

Media Image© Patrick McMullan via Getty Image

Carolyn donned a pair of smart loafers in 1995

Ahead of the pack, in 1995, Carolyn was pictured with actress Jenny Landy, sporting a neatly pressed pair of cropped trousers and a pair of buttery leather loafers - a modern and minimalist approach to footwear.

A crisp white shirt

Princess Diana in Bosnia 1997 wearing jeans and a white shirt

Known as a capsule staple, the humble white shirt will never go out of style, and both Carolyn and Diana executed this look to the full during their lives in the public eye.

Princess Diana often teamed hers with jeans for on-the-go royal appearances, and she made the separate instantly glamorous with gold jewellery.

Media Image© Ron Galella Collection via Getty

Carolyn's take on the androgynous look in 1999

In 1999, Carolyn preferred an androgynous look, styling her white, wide-lapelled shirt with a simple black skirt when she was pictured at a Whitney Museum gala in New York.

More Royal Style
See more