The prevailing theme of this New York Fashion Week so far is that everyone wants to be a preppie now—but prep is a state of mind that Caroline Calloway, the writer, influencer, and estranged NYC socialite, has never quite left.
“There’s nothing I find more inspiring than a reverence in Gothic castles,” Calloway tells me backstage at the J. Press runway show on Thursday. “I’m just so glad that the rest of the world is back on board because I never stopped loving this shit.”
We’re huddled together on a landing of a blue-carpeted stairwell at the Explorers Club, a 121-year-old members-only institution that’s headquartered in a Jacobean revival mansion on Manhattan’s Upper East Side. As we speak, a sound system blasting the Brideshead Revisited score reverberates throughout the multi-floor building, which features wood-paneled walls, oil paintings both nautical and pastoral, and myriad taxidermy animals. Though the show is slated to start in approximately 20 minutes and Calloway is set to model a Yale-branded warm-up parka, a tan cable-knit sweater, and pleated wool trousers, she’s currently wearing a strapless tea-length dress made of pink tulle paired with white Hoka sneakers—a more temperate choice for a warm, stuffy old building.
Calloway is a longtime friend of J. Press’s new president and creative director Jack Carlson, who previously founded the prep-meets-streetwear label Rowing Blazers (she once modeled for them too). The two met, she tells me, “drunkenly in a castle, in white-tie” a decade ago while Carlson was doing graduate work at Oxford University and Calloway was an undergrad at Cambridge. For Thursday’s show, she made the trip up to New York City from her home in Sarasota, Florida, to catwalk for Carlson’s latest venture.
“Besides the fact that my best friend has asked me, a known bohemian layabout, to arrive at a call time of 7 a.m., it’s been absolutely delightful,” says Calloway. “I’ve been meeting the coolest fucking people,” she adds, “although, I will say, I keep making the gaff of leading with, ‘How do you know Jack?’ and people are like, ‘Bitch, I’m a real model. I was hired for this because I model professionally.’ And I’m like, ‘Right, right, right.’”
Since she moved from her storied West Village apartment to a Florida condo in 2022, Calloway published her years-in-the-making memoir, Scammer, in 2023, as well as a second volume, Elizabeth Wurtzel and Caroline Calloway’s Guide to Life, earlier this year.
“It wasn’t that good, don’t read it,” she tells me of her latest tome, “but Scammer was the masterpiece that everyone said, so if you’re gonna buy one, definitely go for the first one. I have two more books coming out this year. They’re small ones, sort of collected things that I’ve already published, but I really have my eye on book five. I think it’s gonna be another Scammer-level masterpiece.”
How’s Calloway’s life in Florida otherwise?
“God, it’s so boring,” she admits. “Nothing happens to me there… My life is just bleached by the sunlight and every day is sunny and it’s like living in a white-cube gallery space, weather-wise.”
I wonder, Does being here make you want to come back?
“Girl, are you kidding me?” she says, though I cannot immediately tell how she means it until she grins. “I yearn. I hunger. I hunger to come back, but I think I want to get a few more books under my belt.”
