Richard Press on J. Press and the art of getting dressed

More than a century after it was founded, J. Press is keeping Ivy League style alive

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Have you noticed that everyone is forever doing his or her own thing these days? Walk down any city street: this person is buried in their phone, that person is wearing headphones and the person over there is smoking some once-illicit substance. Uniformity is out; individuality is in.

This applies doubly — triply? — to styles and standards of dress. Once upon a time, a majority of the public agreed on one way to dress for work, another way to dress for a religious service or wedding, yet another way to dress for a dinner party….

Have you noticed that everyone is forever doing his or her own thing these days? Walk down any city street: this person is buried in their phone, that person is wearing headphones and the person over there is smoking some once-illicit substance. Uniformity is out; individuality is in.

This applies doubly — triply? — to styles and standards of dress. Once upon a time, a majority of the public agreed on one way to dress for work, another way to dress for a religious service or wedding, yet another way to dress for a dinner party. Suits were de rigueur for men in most professions, and, no matter the occasion, women wore gloves, hats, and stockings — not as a marker of social standing, because women from all classes did so, but as an acknowledgment of femininity.

These days, though, no one can agree on what to wear. From sweatpants to skinny pants, puffer jackets to Crocs, suits without ties to suits with sneakers, the sheer variety of ways in which people insult good taste can be simply staggering.

A couple of times each year, though, I am reminded of the dress codes of days gone by when the J. Press catalog arrives in my mailbox. Founded in 1902 by an immigrant from Latvia named Jacobi Press, the men’s clothier laid the foundations for the Ivy League look as the dress style of choice for scores of midcentury businessmen, attorneys and government officials. Simply put, J. Press, with quality and durability, designed and tailored the successful American man’s unpretentious uniform.

From its base of operations in New Haven, Connecticut (the home of Yale University) and its various satellite stores, the retailer survived the fashion nightmares of the last fifty years. Yet it can no longer claim culture-wide influence. Once, J. Press was the brightest star in a veritable constellation of Ivy League-oriented stores: Brooks Brothers, F.R. Tripler, Paul Stuart, and countless smaller-market shops across the country — from O’Connell’s in Buffalo, New York (which still exists) to Woodhouse Lynch in Columbus, Ohio (which does not).

“There was an Ivy League store in most cities throughout the country,” Richard Press, the grandson of Jacobi Press and son of later president and CEO Paul Press, told me in a recent conversation. “It was what everyone chose to wear, whether they went to college or prep school or not.”

J. Press is now the leader of a smaller niche market — an admittedly vibrant one for those who choose to model their style of dress on, say, John F. Kennedy rather than John Fetterman. All the same, Richard Press is undaunted. He turned eighty-five this year, and he has spent most of his life working for — or having an association with — J. Press, most recently as the author of a delightful pair of books recounting his adventures in and around menswear: Threading the Needle, published in 2021, and its recent sequel, Threading the Needle II. He has a seemingly limitless storehouse of insights and reminiscences, and ample reserves of gusto with which to tell them — as I discovered when I called him in April.

“Basically, it’s a natural shoulder,” he says of the fundamentals of the Ivy League suit. “It doesn’t have to be three-button, although J. Press has promulgated the three-button natural shoulder suit. It’s using materials that are softer finish. They’re not hard finish. For winter weight, whether it’s flannel trousers, it’s almost 100 percent woolen or cotton, using very little if any polyester whenever possible.” And he can go on and on — about Oxford button-down shirts, about brushed Shetland sweaters (J. Press’s inimitable Shaggy Dogs are the most unique on the market)…

Richard Press grew up surrounded by these sartorial principles. In 1950, in search of a suit for Richard’s upcoming bar mitzvah, Jacobi Press marched his grandson into archrival Brooks Brothers, where, Richard remembers, his grandfather was bowed to by the employees “as if he were Buddha.”

“He picked out a size twelve gray flannel suit for me,” Richard says. “He said to the salesperson, ‘How much is it? I’ll pay you in cash. Take off the tag.’ And we went back across the street to J. Press, where he tore out the Brooks Brothers label, put the J. Press label in, chalked up, and fitted the suit at J. Press.”

Paul Press dressed within the Ivy League tradition but with a dash of Savile Row panache in his tailoring, his son reports. “He had his own look and it befit him,” Richard says of his father. “He was very close to Yale, even though he didn’t go there.” In fact, Paul Press graduated from the University of Pittsburgh. “At that time, all the Ivy League schools had very strict Jewish quotas,” Richard says. “If he weren’t Jewish, if he were a WASP and had a C+ average, he would’ve been accepted.”

Richard is both a clotheshorse and a showman. “Growing up in New Haven, I went to all the openings of all the tryouts, which all opened in those days at the Shubert Theatre,” he says. At the Loomis Chaffee School, he appeared in school productions, and by the time he made it to Dartmouth College, he co-authored a musical. “I had a fraternity brother, Larry Elliott, who was the head of the Dartmouth Indian Chiefs — an unlikely name nowadays — a Dixieland band,” Richard says. “We wrote a musical comedy that won an award and was performed before the whole college.”

Although he has worked as an actor, when he began drawing a paycheck at J. Press, Richard applied his theatrical flair to paying and prospective customers. “I performed as if I were on the stage when I was on the floor of J. Press, running the New York store,” he says. “Anytime I greeted anyone, the curtain went up.”

And, during its peak years in the Fifties and early Sixties, J. Press attracted quite an audience. “We had a lot of theatrical movie stars who were customers of J. Press — Sinatra, Walter Matthau, Cary Grant for a couple of years,” Richard remembers, but even among the non-rich and less-than-famous, there was demand for the Ivy League look. “When FDR’s GI Bill of Rights was enacted, veterans who were public-school high-school graduates entered in droves to the Ivy League,” he says, and the new enrollees adopted the look of the “so-called elite.” The in-crowd dressed like this because they were in the in-crowd; everybody else dressed like this because they wanted to be perceived as being in the in-crowd. But then a democratization took place. “They got their, say, J. Press blue blazer or tweeds on sale, and they wore them with their Army khakis,” Richard remarks. “The Skull-and-Bones elite fence club guys at Yale took to that.”

The Vietnam War era brought the curtain down on the widespread appeal of traditional menswear. Richard has a theory: loyal adherents of the J. Press/Brooks Brothers style no longer wanted to dress in the manner that suggested conservatives like William F. Buckley Jr. “They went to the more ragged rags-and-bones style,” he says. By the 1980s, high style (or, at least, expensive clothes) mounted a comeback, but it was glitzier, snazzier, flashier than what had come before. “Armani came in, and various looks,” Richard says. What about Ralph Lauren? “He adapted some Ivy League in terms of the type of materials he would use,” Richard comments. “But his look, the tailoring, was really much more Savile Row. It didn’t have a natural shoulder. It didn’t have the particular peculiarity that denoted the Ivy League style.”

Brooks Brothers continued on — as it does, in its latest of many permutations, to this day — but it made concessions to modern tastes. “Brooks Brothers, to facilitate an urban, more corporate image, sold more dark blue suits, where J. Press sold very few — mostly gray and lighter colors and much brighter looks,” Richard says.

Nowadays, however, suits of any kind worn by men are rarer than hen’s teeth. “I’m not optimistic about the advancement of good taste and culture within American society right now,” says Richard, who, wearily, points to a recent notice for a memorial service that included a distressingly obvious request. “It said, ‘Males attending the memorial service are asked to dress appropriately with a coat and a tie,’” Richard says. “That bespeaks the age.” When he’s out and about in New York, he says, about “one in thirty” men are in a coat and tie.

Nevertheless, J. Press has persisted. Owned for several decades by a Japanese concern called Onward Kashiyama, J. Press still operates brick-and-mortar stores in New Haven, New York and Washington, DC, and reaches the broader public through the mail and online — the way traditional-minded dressers living in the sticks get their duds. Salesmanship elsewhere may be “gone with the wind,” Richard says, but “it’s not gone at J. Press.”

After leaving J. Press in 1991 to run the now-defunct F.R. Tripler in New York and then decamping to Florida, Richard was coaxed back to the family business some years ago. “I ended up as an emcee at all their events,” he says. He began penning weekly (then biweekly) online columns that formed the basis for Threading the Needle. Undoubtedly the company’s digital business has been aided by his advocacy and passion. Plus, there are still jobs out there that require grown-ups to dress like grown-ups, especially in the nation’s capitals. “So many J. Press customers work in government, administration, they’re judges, and they have to wear a suit,” he says. At least someone still does.

But enough about dressing for work. The weather is warming up; summer is upon us. Let’s say you are a young man under forty. What do you wear in the months ahead? Let’s ask the expert: “If he lives in a more formal geographical location — i.e., urban or top-grade suburban, and if he was going to a wedding — I should say maybe a linen suit, a seersucker suit, a madras jacket with white slacks.”

One senses that Richard Press relishes dispensing such advice. “At this time of my life,” he says, “to be so very actively involved truly keeps me going, along with the gym and my dirty martini every night.”