Meet the Designer Who Styled Jason Schwartzman’s White Socks-and-Loafers ‘Tonight Show’ Look

F.E. Castleberry espouses an eclectic yet precisely tailored aesthetic that’s drawn comparisons to the films of Wes Anderson. So, it was something of a meta moment when the indie designer found himself dressing frequent Anderson player Jason Schwartzman days before the latter’s August 21 ^st Tonight Show appearance .

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“In some ways it felt a little surreal, but in other ways, quite fitting,” says Castleberry, who attired the Rushmore star in a navy mohair-blend suit , a two-tone, blue striped shirt with an oversized club collar, black lugged bit loafers from his own label, and a vintage Hermes tie. The surprise finishing touch was a pair of “freshly laundered” Adidas by Wales Bonner beige cotton socks that Castleberry plucked from his own drawer when the actor realized he was bereft of socks to pair with the suit just hours before the taping.

“Being a huge music fan, he understood that reference, which is why I thought it was such a great fit,” Castleberry says of the white-athletic-socks-with-a-suit look, which had previously been practiced by Michael Jackson and Fred Astaire.

It was the denouement of a drama that had begun two weeks earlier, when Schwartzman’s stylist Rose Forde tapped Castleberry to dress her client for his Fallon spot. The two initially met at Castleberry’s Tribeca atelier outside of its regular operating hours, with the designer feeling a slight case of the butterflies.

“I think I had some nerves before our meeting, because several of the films that he stars in are some of my favorite films of all time,” Castleberry tells Robb Report, citing Rushmore and The Darjeeling Limited in particular. “Those films have significantly influenced various design decisions that I’ve made in the past and present, and they make me fall in love with tailored clothing every time I watch them.”

After breaking the ice by discussing Weezer’s Blue Album and reading American Psycho, Castleberry responded to the actor’s enthusiasm for a suited look and curated Schwartzman’s tailored ensemble. He even accompanied Schwartzman to the taping itself, where Castleberry could be on hand to set his tie to the properly jaunty angle. Castleberry’s efforts were ultimately rewarded by Fallon’s first words to Schwartzman in the interview: “Looking sharp!”

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Whether they have an appointment at 30 Rockefeller Plaza or not, Castleberry encourages men who wear tailoring by choice to do so with a greater sense of “ease.” Think wider trouser legs, longer jackets, and broader lapels—all design decisions that can deflect a suit from looking corporate or court-mandated.

“If you’re going to choose to wear a suit, I would introduce more ease into the silhouette, to pay homage to where tailored clothing is headed,” he says. “Everything’s loosening up a little bit.”

But equally important is how tailoring is worn.

“It’s like that line in The French Dispatch, ” says Castleberry, citing another Anderson-Schwartzman collaboration. “Bill Murray says to the writer, ‘Try to make it sound like you wrote it that way on purpose.’ Just wear the suit like you put it on on purpose.”

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