Calvin Klein’s ex recalls ‘last day’ with Carolyn Bessette Kennedy

Calvin Klein’s ex-wife Kelly Klein remembered the ‘last day’ she saw Carolyn Bessette before her and husband John F. Kennedy Jr.’s tragic death nearly three decades ago.

Kelly became close friends and colleagues with Bessette during the late icon’s nearly eight years working for the luxury label during the late 1980s to the mid-1990s.

Bessette famously served as a Calvin Klein sales ᴀssociate before rising the ranks at the brand’s NYC headquarters as a fashion publicist who catered to VIP clients.

Three years after Bessette left the company in 1996 amid her highly publicized romance with JFK Jr., the married couple died in a plane crash while en route to a Kennedy family wedding on July 16, 1999. Bessette was 33 and Kennedy was 38.

Ahead of the 27th anniversary of their untimely deaths, Kelly took to Instagram on Wednesday to remember the ‘elegant’ Bessette, who she said is ‘greatly missed.’

In the post, Klein’s wife of 20 years revealed that she saw Bessette for the last time just one day before the 1999 tragedy that shocked the world.

Calvin Klein’s ex-wife Kelly Klein recalled the ‘last day’ she saw the late Carolyn Bessette before her and husband John F. Kennedy Jr.’s tragic death; Bessette and Kennedy seen in 1997

Kelly (seen with Klein in 2025) became close friends and colleagues with Bessette during the late icon’s nearly eight years working for the luxury label during the late 1980s to the mid-1990s

‘I didn’t know today would have been the last day I saw you!’ Kelly began. ‘If you only knew what was going on down here!’

Kelly, writing directly to her late friend, marveled at how Bessette has ‘influenced so many of our young generation in only the most positive ways.’

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She continued: ‘Simple elegant minimal style! Just you and your natural being. Rest in peace Carolyn ! You are greatly missed !’

Kelly concluded her tribute by revealing the backstories behind the two pH๏τos of Bessette that she chose to include in Wednesday’s post.

The first pH๏τo, which was a candid outdoor sH๏τ of Bessette walking through a tunnel in a white blouse with a sweater tied around her waist, was taken during ‘a trip to Paris,’ according to Kelly.

The second sH๏τ was a polaroid of the blonde beauty modeling a yellow slip dress during ‘a fitting [Kelly and Bessette] were doing for [Calvin Klein]!’

The Daily Mail has reached out to Kelly’s representatives for comment but has yet to hear back. 

Kelly worked closely with Bessette at Calvin Klein in the 1990s while serving as her designer husband’s ‘muse’ during their two decades of marriage from 1986 to 2006.

This is not the first time that Kelly, who now works as a pH๏τographer and artist, has publicly mourned Bessette’s pᴀssing.

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Ahead of the 27th anniversary of their untimely deaths, Kelly took to Instagram on Wednesday to remember the ‘elegant’ Bessette, who she said is ‘greatly missed’

In the post, Klein’s wife of 20 years revealed that she saw Bessette for the last time just one day before the 1999 tragedy that shocked the world; Bessette (L) and Klein (R) seen in 1994

Kelly, writing directly to her late friend, marveled at how Bessette has ‘influenced so many of our young generation in only the most positive ways’; Bessette seen in March 1999

On July 16, 2020, Kelly honored the 21st anniversary of the plane crash that claimed the lives of both Bessette and JFK Jr. on Instagram.

She posted a black and white throwback pH๏τo of herself and Bessette smiling with their arms wrapped around one another.

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The caption of her post included several hashtags, including #throwbackthursday and #berlinwall.

She also tagged modeling agent Paul Rowland as well as a now-deleted Carolyn Bessette Kennedy Instagram page.

Bessette first began her career at Calvin Klein back in 1988 after a life-long fascination with the fashion industry.

She got a job as a sales ᴀssociate at a Calvin Klein store in Newton, Mᴀssachusetts after earning a degree from Boston University in elementary education.

Bessette was soon discovered on the job by a Calvin Klein higher up, who recommended her to headquarters in New York City amid an active search by then-president Susan Sokol to find a salesperson who could work with celebrity clientele.

She eventually landed the once in a lifetime gig and quickly began catering to the likes of A-list actress Annette Bening and even legendary journalist Diane Sawyer.

‘She entered the fashion world like Venus coming up out of the ocean. Calvin saw it immediately,’ the brother of Calvin Klein former creative director Zack Carr previously told People. ‘Everyone was talking about her.’

Bessette famously worked as a Calvin Klein sales ᴀssociate before rising the ranks at the brand’s NYC headquarters as a fashion publicist who catered to VIP clients; Bessette and Klein seen in 1992

Bessette backstage with a model at the Calvin Klein 1994 ready-to-wear show in New York’s Bryant Park

Kelly was married to Calvin Klen (seen together in 1992) from 1986 to 2006 and famously served as the designer’s ‘muse’

After proving herself as a celebrity salesperson, Bessette continued to move up at the company.

She worked as the brand’s PR director before reportedly becoming ‘show production director.’

After nearly eight years at the company and just months before she married into American royalty, Bessette parted ways with Calvin Klein in 1996.

Bessette’s rise at Calvin Klein as well as her and JFK Jr.’s doomed relationship is depicted in the 2026 Hulu series Love Story, which was released earlier this year and sees actors Sarah Pidgeon and Paul Anthony Kelly play the late couple.

The nine-part drama follows Kennedy and Bessette’s relationship, from the two meeting at a party to the deaths of the couple and her sister Lauren Bessette (Sydney Lemmon) on July 16, 1999. 

They all died when a small plane piloted by Kennedy crashed into the Atlantic Ocean near Martha’s Vineyard en route to his cousin Rory Kennedy’s wedding.

The series synopsis reads: ‘It was a love story that captured the attention of the nation: John F. Kennedy Jr. was the closest thing to American royalty. The country watched him grow from a boy to a beloved bachelor and media sensation. 

‘Bessette was a star in her own right. Fiercely independent and with a singular style, she rose from being a sales ᴀssistant to an executive at Calvin Klein and became a trusted confidante of its eponymous founder. 

‘John and Carolyn’s connection was immediate, electric and undeniable. As their love story unfolded on a national stage, the intense fame and media attention that came along with it threatened to rip them apart.’

Love Story sparked much backlash from several of the people depicted in the show as well as from the friends and family members of the late couple. 

JFK Jr.’s nephew Jack Schlossberg slammed executive producer Ryan Murphy for ‘making millions’ off his uncle’s legacy in a ‘grotesque’ way and for allegedly never consulting the family about his plans for the series.

‘If you want to know someone who’s never met anyone in my family – knows nothing about us – talk to Ryan Murphy,’ Schlossberg fumed on CBS Mornings.

Three years after Bessette left the company in 1996 amid her highly publicized romance with JFK Jr., the married couple died in a plane crash while en route to a Kennedy family wedding on July 16, 1999. Bessette was 33 and Kennedy was 38; seen in May 1997

Bessette’s rise at Calvin Klein as well as her and JFK Jr.’s doomed relationship is depicted in the 2026 Hulu series Love Story, which was released earlier this year and sees actors Sarah Pidgeon an Paul Anthony Kelly play the late couple

‘The guy knows nothing about what he’s talking about and he’s making a ton of money on a grotesque display of someone else’s life.’

Schlossberg has called on Murphy to donate his proceeds from the show to ‘some of the causes that John championed throughout his life’ or ‘to the JFK Library to help keep President Kennedy’s memory alive’.

And he has taken the producer to task over not following through, saying: ‘You’re making millions off John, making a public spectacle of it but won’t contribute any of your riches to the causes he championed, or the legacy of public service he represented.’

Murphy hit back by claiming that Schlossberg didn’t have a right to be cross because he had been only six years old when his uncle’s tragic death captivated the nation, saying it was an ‘odd choice to be mad about your relative that you really don’t remember.’

But Schlossberg quickly reʙuттed that notion, taking to Instagram to respond: ‘Hey @ryanmurphyproductions: My earliest memories are of John calling me Jackolatern and ‘the nudist,’ picking me up from school, his Pontiac convertible.

‘I remember being the ring bearer at his wedding and the day he died. I remember Wyclef [Jean] singing at his funeral. 

‘More memories are pᴀssed down from stories — like the time he locked himself out of a car in an intersection and asked the guy screaming at him if he could borrow a golf club to smash the window to get the keys, and then did it.’