The Eternal Enduring Style of JFK Jr.

LONDON — John F. Kennedy Jr. has become an accidental poster boy for tennis and sportswear.

In Luca Guadagnino’s latest film “Challengers,” starring Zendaya and Josh O’Connor, Kennedy Jr. was a direct inspiration for designer Jonathan Anderson, who designed the costumes.

“When JFK Jr. was younger, in the ‘80s and ‘90s, there was kind of an effortlessness to his wardrobe — like he could wear anything, and sex appeal would always be there,” the designer told WWD.

“I felt like [Patrick Zweig, the character played by O’Connor] should not care how he looks because, ultimately, he is not endorsed, he is not the biggest star in tennis, so his look becomes a bit ad-hoc and stuck together. But when you look at the base parts of his attire, he has very aged, expensive things, including an old wallet that’s still very expensive, though it’s falling apart,” Anderson added.

JFK Jr.’s Best Style Moments: A Look at His Effortlessness & Timeless Sex Appeal

John F. Kennedy Jr. in his robe at his graduation from Brown University.

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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 Jr.’s own T-shirts that he wore in his heyday.

At the Rome premiere, Anderson wore the T-shirt that’s most similar to Kennedy Jr. and Zendaya. The designer recreated a formal version in a pleated shirt for O’Connor to wear to the London premiere.

“JFK Jr. is indeed one of those characters you will often gravitate toward as a style source; more so for his casual sporty looks than for his formal attire. His holiday looks with wider-cut slacks, sweaters and sport shirts are classic in the true sense of the word. He is definitely one of the historic figures within politics that clients might reference,” said Dag Granath, cofounder of Stockholm-based tailoring brand Saman Amel, which will open its first brick-and-mortar store in London’s Mayfair on 17 Albemarle Street next month.

JFK Jr.’s Best Style Moments: A Look at His Effortlessness & Timeless Sex Appeal

John F. Kennedy Jr. in 1988.

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The Kennedys are America’s version of the British royal family. Each family member is always immaculately dressed in sharp tailoring and they are often involved in scandals, conspiracy theories and or even so-called curses.

When the family lived in the White House, John F. Kennedy and his wife, Jackie would clash over their son’s hairstyle. His father wanted him to keep it short, meanwhile his mother urged him to grow it long, like the Beatles.

JFK Jr.’s Best Style Moments: A Look at His Effortlessness & Timeless Sex Appeal

John F. Kennedy Jr. attends the U.S. Open Tennis tournament in 1991.

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“John quickly became a trendsetter in young boys’ fashion, usurping the spot formerly held by Prince Charles, heir to the British throne. Mothers across the country took their young boys to barbers and insisted on the ‘John-John,’” wrote Steven M. Gillon, friend of Kennedy Jr. and author of “America’s Reluctant Prince: The Life of John F. Kennedy Jr.”

Kennedy Jr. remains on trend and on mood boards even 25 years after the tragic plane crash where he died along with his wife, Carolyn Bessette and sister-in-law, Lauren.

The Old Money aesthetic, a style reserved for legendary American families such as the Vanderbilts and Gettys, has also been populating on TikTok, accumulating more than 130 million views, as well as on Instagram, where the hashtag has amassed more than 385,000 posts.

“[JFK Jr.’s style] ties in well with Lady Di’s style or the ongoing obsession with all things Aimé Leon Dore coded and relating back to a New York preppiness,” said Peter Bevan, a London-based stylist.

JFK Jr.’s Best Style Moments: A Look at His Effortlessness & Timeless Sex Appeal

John F. Kennedy Jr. with his injured hand wrapped in a bandage with Carolyn Bessette Kennedy in 1997.

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Kennedy Jr.’s nephew, Jack Schlossberg, has been compared to the late attorney, journalist and magazine publisher, in his charm and outdoorsy nature.

“While it feels a touch more manicured, Jacob Elordi [the Australian actor who starred as Elvis Presley in the ‘Priscilla’ film] has elements of JFK Jr. about him, when he’s spotted reading at a petrol station in a vintage Disney sweatshirt and jeans. He has the same sense of thrown together elegance that JFK Jr. had,” Bevan added.

Sasha Chermayeff, one of Kennedy Jr.’s closest friends, describes his 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.”

The relaxed, slouchy look popularized by Giorgio Armani for the film “American Gigolo,” was just coming into style as Kennedy Jr.’s popularity grew.

JFK Jr.’s Best Style Moments: A Look at His Effortlessness & Timeless Sex Appeal

John F. Kennedy Jr. in 1993.

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“He very neatly amalgamated his athleisure physique and lifestyle with his dresswear. At the time in the ‘90s, it was definitely becoming more of a style factor for people to incorporate techy sportswear with their casual attire, or with slacks,” said Sunita Kumar Nair, author of “CBK: Carolyn Bessette Kennedy: A Life in Fashion.”

“What made him stand out was that he managed to relay this kind of debonair, jetset aesthetic, which, to my mind, I think about Edoardo Agnelli. It’s this very relaxed, but formal attire, but done in this very American way, which stands out amongst other kinds of American wear. It’s almost Italian, but he was never without a necktie on his formal attire,” she added.

JOHN JOHN KENNEDY RELAXING IN CENTRAL PARK (Photo by Lawrence Schwartzwald/Sygma via Getty Images)

John F. Kennedy Jr. in Central Park.

Sygma via Getty Images

There was also a European sensibility to Kennedy Jr.’s style. In the late ‘60s, when Jackie married Aristotle Onassis, her moniker Jackie O was coined by WWD, the family went to live on the private island of Skorpios in Greece.

“[The Kennedys] represent this golden age of youth, vitality, charisma, intelligence, talent, beauty and sophistication. They have these family heirlooms that have weight and gravitas to it,” explained Nair, alluding to Kennedy Jr. keeping some of his late father’s neckties and a watch.

“He’s the sort of embodiment of that really laid-back elegance that’s arch preppy — in that very relaxed way that only the very rich or the very powerful can get away with dressing,” said Patrick Grant, director of the Savile Row business, Norton & Sons.

JFK Jr.’s Best Style Moments: A Look at His Effortlessness & Timeless Sex Appeal, Photos

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