The J. Press Madison Avenue expansion marks a turning point for a clothier that, as recently as 2024, operated just three stores in the United States, including its original outpost on New Haven’s Elm Street, according to the Yale Daily News. Later this month, a new flagship opens at the corner of Madison Avenue and East 44th Street in Manhattan, and the brand intends to follow it with as many as 20 new American stores over the next four years, pushing annual sales tenfold to $100 million.
The flagship’s wood panels, old photographs, and letters from former American presidents set a particular tone: reverential, unhurried, confident in the weight of its own history. It is also, in a quiet way, a territorial statement. The Brooks Brothers building, built in 1915 as the flagship of J. Press’s more famous Ivy League rival, stands directly across the street and has sat empty since Brooks Brothers filed for bankruptcy in 2020. Jack Carlson, J. Press’s creative director and president, was finalising a deal to take over that very building when it was sold from under him.
From three doors to twenty: the scale of the J. Press Madison Avenue expansion
Carlson is not a newcomer to ambitious brand-building. He founded Rowing Blazers, a prep revival label, before selling it to Burch Creative Capital in 2024, according to Onward Holdings, the Japanese clothing group that owns J. Press. Onward also notes that Carlson led the revival of Warm & Wonderful, a knitwear label beloved by Diana, Princess of Wales. That combination of heritage instinct and commercial track record is, presumably, what persuaded Onward to hand him the keys to a 125-year-old institution.
The scale of what he is attempting is not lost on him. ‘I’m not trying to be flippant about it, but $100 million is not a massive company,’ he says. ‘That’s where we probably should be, if J. Press and Ivy style matter in the conversation.’ The fashion business has a long memory for brands that overreached: the crumbling Brooks Brothers building is right there to remind him.
J. Press was founded in 1902 by Jacobi Press, a Jewish immigrant from Latvia who opened a tailoring shop on the Yale campus. Over the following decades it became a chief purveyor of Ivy League style, name-checked by F. Scott Fitzgerald and Tom Wolfe, and worn by figures including Cary Grant, Miles Davis, and John F. Kennedy. The brand remained family-owned until 1986, when it was sold to Onward Holdings, which had been licensed to sell J. Press in Japan since the 1970s. Onward now operates 80 J. Press stores in Japan, where Ivy style has been popular since the 1960s.
Shaggy Dogs, Shetland wool, and the question of quality at scale
Carlson’s strategy is to grow by doubling down rather than diluting. The Shaggy Dog sweater, a Scottish wool crewneck named for its brushed surface, now comes in more than 75 styles and colours. Each one is still hand-brushed in the Shetland Islands by a craftsman named Ian, using a teasel made from the head of a local flower. Ian’s grandfather held the same job before him. With demand rising, the factory has been running around the clock. Carlson’s answer is not to move production. ‘It’s growing the factory and growing the capacity right there in Shetland,’ he says. ‘Ian’s going to have to have a friend sitting next to him with more teasels.’
Fabric choices elsewhere in the collection point in the same direction: Fox Brothers flannel, Barbour waxed cotton, Fair Isle knits. Will Eaton, moderator of r/NavyBlazer, a Reddit community devoted to Ivy style, is cautiously positive. ‘Generally, I think J. Press is headed in the right direction,’ he says, noting Carlson’s plans to revamp Oxford shirts for a better collar roll and his use of cloth from Fox Brothers.
The brand’s first New York Fashion Week show earlier this year, built around the canonical menswear book Take Ivy, drew mixed reviews. The sharpest came from Tyler, The Creator, who questioned on Instagram whether the collection was distinctive enough. Tyler later walked back his comments, and Carlson sent a peace offering: a limited-edition version of the show’s centrepiece, a $1,500 blaze orange waxed cotton raincoat made to order in a run of five. ‘You’re always going to have the real fashion guy who was hoping for something way more avant-garde, and you’re always going to have the self-appointed reactionary guy whose personal definition of Ivy is the be-all and end-all,’ Carlson says. ‘I’m not going to be too hung up on what Tyler or anybody else might say, but I’ll certainly invite Tyler to the show, and I hope he comes.’
His sophomore New York Fashion Week presentation expanded the brief, introducing J. Press’s first women’s collection in 50 years alongside the classics. A cast diverse in age and ethnicity walked the runway, reflecting the brand’s stated intention to take what was once the exclusive territory of wealthy East Coast WASPs and open it to a wider audience. Carlson traces that inclusive instinct back to the founder himself. ‘Jacobi Press came to America from Latvia and he didn’t grow up with any of this British stuff,’ he writes. ‘He was kind of the Ralph Lauren of his day, he created an idealized version of the world he imagined at Cambridge and Oxford, and on great British country estates.’
W. David Marx, author of Ametora: How Japan Saved American Style, remembers walking past the J. Press shop in Cambridge on his way to class at Harvard. He argues that broadening the audience is overdue. ‘J. Press was fundamental to the creation of the original Ivy League style, and I’m excited to see it play a role in defining the much broader and more inclusive idea of Ivy League style for this century,’ he says. The J. Press flagship on Madison Avenue opens later this month, with the full 20-store build-out planned over the following four years.
