Kennedy Grandson Jack Schlossberg ‘Recommends’ Being a Kennedy, Talks Nancy Pelosi’s Prom Dress and Voting on ‘Jimmy Kimmel’

Jack Schlossberg, grandson of late President John F. Kennedy and Jacqueline Kennedy, looked dashing in Saint Laurent on Tuesday during a “Jimmy Kimmel Live!” appearance.

The writer and political correspondent looked svelte in all-black, wearing a slim-cut gabardine jacket and trousers, poplin shirt and leather chelsea boots. Schlossberg kept accessories to a minimum, wearing a cord bracelet on one wrist, and a leather watch on the other.

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jackie kennedy and jfk's grandson, kennedy family, Jack Schlossberg wore Yves Saint Laurent for his "Jimmy Kimmel Live!" appearance, carolyn kennedy son.
Jack Schlossberg wore Saint Laurent for his “Jimmy Kimmel Live!” appearance on Sept. 24.

His TV stint came hours after Saint Laurent’s spring 2025 show on Tuesday, where Anthony Vaccarello showed a collection based around the suits of designer Yves Saint Laurent, and the wardrobe of his muse Loulou de la Falaise.

“I wanted to mix it up,” Vaccarello told WWD just before the show. “Saint Laurent is a ready-to-wear house, known for its jackets, for its suits — real pieces of everyday life. And I wanted to pay homage this season.”

Schlossberg has become a social media sensation thanks to his all-American good looks, canny sense of humor and activism.

On the show, Kimmel discussed the Kennedy legacy of public service, to which Schlossberg quipped he “recommends” being a Kennedy.

Kimmel presented a side-by-side photograph of Schlossberg’s meeting with Nancy Pelosi, comparing it to a photo of his grandfather meeting Pelosi in her younger days. “She told me it was her prom dress that she wore to meet my grandfather. It was an honor to meet her at the DNC,” Schlossberg said.

He also addressed his uber-viral TikToks, including one from July with David Letterman and second gentleman Doug Emhoff. In it, the trio played a game of Schlossberg’s own creation, “Condiment or Sauce,” debating whether dips, like ketchup, qualified as condiments or sauces.

Kimmel got in on the action, discussing the status of ranch dressing and barbecue sauce. He also teased Schlossberg’s tendency to put mayonnaise on pizza.

jackie kennedy and jfk's grandson, kennedy family, Jack Schlossberg wore Yves Saint Laurent for his "Jimmy Kimmel Live!" appearance, carolyn kennedy son.
Jack Schlossberg wore Saint Laurent for his “Jimmy Kimmel Live!” appearance on Sept. 24.

“The only thing more important than mayonnaise to me is showing up to vote in this election,” said Schlossberg, to which Kimmel replied: “That’s one of the most skillful segues I’ve ever heard. Your grandfather would be very proud.”

Kimmel’s right — Schlossberg’s no dilettante.

Following the footsteps of his maternal grandfather, Schlossberg graduated from Harvard Law School in 2022, with a joint Juris Doctor and Master of Business Administration qualification. Prior to that, he attended Yale University, where he studied history with a focus on Japan.

The writer recently spoke during the second night of the Democratic National Convention in Chicago, along with other speakers including former President Barack Obama and First Lady Michelle Obama, as well as CNN correspondent Ana Navarro.

Jack Schlossberg’s Style Over the Years: A Look Back at Caroline Kennedy’s Son, Photos

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Launch Gallery: Jack Schlossberg's Style Over the Years: A Look Back at Caroline Kennedy's Son, Photos

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