There’s a navy sweatshirt in the new J. Press collection with a phrase knitted into it in off-white yarn: Old enough to know better.

The OLD part takes care of itself. J. Press is the 123-year-old outfitter that’s kept men in pants and loafers through World Wars, depressions, and revolutions. The Kennedys loved it, as did Roosevelt, Ford, Clinton, and both Bushes. Miles Davis wore its patch-pocketed blazers, Frank Sinatra liked its button-down oxford shirts, and George Plimpton was fond of the “shaggy dog” sweaters.

Set up by Latvian immigrant Jacobi Press in New Haven in 1902, J. Press found its niche in those incoming Ivy League boys who wanted now to be Ivy League men—and who landed, perhaps, somewhere in the middle. It’s a sort of endless stylistic adolescence; a school uniform for life; the buttoned-up, un-buttoned look that came to define what would later be called “Ivy style” or “prep,” but which several decades of men of a certain stripe simply called “getting dressed.”

As for the knowing better part—well, that’s harder to pin down. That whiff of rakishness, of high jinks, of capers and romps—this is the unspoken atmosphere in which J. Press (and, come to think of it, the entire preppy canon) exists. “The better you dress, the worse you can behave” sort of thing—which might be the unofficial motto for the British aristocracy, from whose wardrobes many preppy brands have descended. (The Duke of Devonshire knit one that read: Never Marry a Mitford.)

Statement knitwear is an important part of the program.

J. Press has been owned by the Japanese brand Onward Kashiyama since 1986. Much has been written on Japan’s late-20th-century obsession with American men’s wear, and in particular the style of the East Coast and the Ivy League. David Marx’s Ametora: How Japan Saved American Style tracks how Japanese youth culture adopted the Aibii look (an interpretation of Ivy League style) in the decades following the Second World War. They applied a degree of reverence, exactness, and craftsmanship that kept the American sartorial code alive, even as standards were slipping in the United States. But the 1964 photography book Take Ivy is the bible to this particular sect. It was consumed widely by Japan’s style-conscious baby-boomers before it was noisily rediscovered by the men’s-wear blogging community of the early 2010s. Compiled by a group of young Japanese photographers, Take Ivy captured the everyday lives and styles of Ivy League students with an outsider’s candor and clarity. Now, in a nicely circular moment, it is widely used by Western designers as a mood board for their own preppy creations.

Brands of J. Press’s age need the occasional sprucing-up. Enter Jack Carlson, its new president and creative director, who describes the house’s golden formula as “authenticity plus irreverence.” “You can find a million brands out there that have one,” he says, “but to have both is extremely special.”

At Rowing Blazers, which he set up in 2017 and sold to Burch Creative Capital last year, he became known for his kaleidoscopically referential designs. Some of them resurrected long-forgotten fashion moments from yesteryear, such as the “black sheep” sweater memorably worn by Princess Diana, which was released in collaboration with its original manufacturer, Warm & Wonderful.

President John F. Kennedy wore J. Press aboard the U.S. Coast Guard yacht Manitou in 1962.

Others came from unlikely collaborations with the estates behind Babar, Tintin, and Paddington Bear. An early partnership with Harry’s New York Bar in Paris on shirts, a hat, and an ashtray foreshadowed many luxury houses’ current obsessions with old-world European restaurants.

In 2017, when Carlson was starting out, friends in fashion warned him not to launch a preppy brand, but it’s hard to see him doing anything else. He studied at Georgetown and Oxford and was heavily involved in the rowing clubs at each, ultimately coxing for the U.S. national rowing team.

He collects old club ties, and with the faraway stare of a man counting days at war, he confirms that they number in the “high thousands.” One is a classic from the J. Press archives, dotted with little yellow grasshoppers. The story behind its popularity is a typical J. Press yarn. When a Yale student out on a date was asked, sometime around the second malted milk, if he belonged to an all-important secret society, he could point to his new J. Press tie and proudly claim allegiance to the fictional “Grasshopper.”

For all its patrician wardrobing, J. Press has always been, perhaps, a club for the just-about-clubless—the outsider’s insider. The company’s ties are made in a factory in Queens by the same man who has been cutting them for more than 50 years.

Carlson’s first collection was unveiled on Thursday at New York Fashion Week, and he is particularly excited about a pair of cords in a very precise shade of pumpkin. The navy blazer will be a three-button, soft-shoulder number with a center hook vent. “And it will have a patch pocket on the chest,” he says triumphantly.

The company’s ties are made in Queens by the same man who has been cutting them for more than 50 years.

Very early on in his tenure, Carlson spent an entire day agonizing over the correct roll of the oxford collar, looking at past and current examples next to photographs of Plimpton and William F. Buckley.

What makes a perfect collar roll? “Entire books could be written about this,” he says. But like that old description of pornography, he adds, usually “you just know it when you see it.” What no one had thought to do, however, was to measure the horizontal space between the two collar buttons.

“People hadn’t factored this into the whole equation,” he says, describing how he spent hours and hours on this task when he first joined the company. “Everyone thought I was crazy.”

“But we’ve got to get stuff like that really, really right,” he says. All so the J. Press man can get it just a little bit beautifully wrong.

Joseph Bullmore is a Writer at Large at AIR MAIL and the editor of Gentleman’s Journal in London