EXCLUSIVE: JFK Jr.’s Clothing Auction Has It All — Calvin Klein, Armani and a Love Story Between the Threads

LONDON — For the first time ever, items of clothing that formerly belonged to John F. Kennedy Jr. will go under auction at Bonhams in New York.

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The online auction will include pieces of clothing worn and owned by the son of President John F. Kennedy and First Lady Jacqueline Kennedy, such as a Calvin Klein tuxedo, two-piece suit and black tie, as well as a Giorgio Armani overcoat, all from the ‘90s.

The sale will coincide with the auction of Jackie O’s Valentino wedding dress between Sept. 16 and 26.

Kennedy’s pieces have a starting estimate of $2,000 to $3,000, but will likely fetch triple that price, if not more.

The Calvin Klein pieces trace back to the start of the attorney, journalist and magazine publisher’s relationship with his future wife, Carolyn Bessette , a Calvin Klein staffer whose specialty was VIPs. The pair met in 1992 at the VIP fitting room of the American brand.

The pieces are being offered up by Sasha Chermayeff, a childhood friend of Kennedy’s; the couple were godparents to her children.

Marissa Speer, Bonhams’ head of sale for handbag and fashion, worked with Chermayeff on the sale of Bessette Kennedy’s black silk wrap trench dress from Yohji Yamamoto’s spring 1998 collection, which also marked the first time an item of clothing from Bessette Kennedy’s wardrobe went up for auction.

The dress sold for $8,960 — nearly quadruple the pre-auction estimate of $3,000.

“Bonhams did so well with the Carolyn piece that Sasha felt comfortable enough to offer up [Kennedy’s pieces]. Sasha was along for every step of the way,” said Speer.

“There’s a love story inside these clothes that I think is just so special. The trenchcoat is purely just JFK Jr., it’s chill, relaxed and casual, but also elegant at the same time,” she added.

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The black suit and tuxedo were part of Kennedy’s formal uniform when he was attending charity galas and openings.

It’s hard to distinguish which events he wore them to, but according to Chermayeff, she describes Kennedy’s style as “schleppy” in Gillon’s book, adding that, “Everything was falling off. He would never even dream of having a pair of matching socks.”

Speer believes that Bessette Kennedy and Jackie O had a big influence on Kennedy’s style.

“The fabrics that Italian designers were using at that time were just absolutely unmatched. Carolyn, working at Calvin Klein, obviously played a huge influence on him and the brand was the American designer of the ‘90s and Jackie’s influence on him was through these beautifully tailored pieces that have lasted forever,” she added.

Kennedy’s style is having a resurgence of its own, the same way his late mother and wife have continued to do so.

In Luca Guadagnino’s film “Challengers,” Kennedy was a direct inspiration for Jonathan Anderson , who designed the costumes.

In the film, Zendaya’s character Tashi Duncan, a former tennis prodigy turned coach, wears a T-shirt that reads “I told ya,” based on one of Kennedy’s own T-shirts that he wore in his heyday.

“His style has a very heavy influence on menswear today and we’re seeing it on red carpets too — it’s more relaxed and fun with a ‘90s edge to it. He would run around New York with his little short shorts and he was one of the kings of street style before there was men’s street style,” said Speer.

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