Interview with J. Press President & Creative Director Jack Carlson

Ivy Style editor and publisher Matthew Longcore had the opportunity to interview J. Press president and creative director Jack Carlson. Here is the transcript from the interview.

Matthew Longcore:

You hold a doctorate in archaeology from Oxford. This is a somewhat unusual background for an executive in the clothing industry. And yet there may be a common denominator between these two seemingly disparate interests. Your doctoral dissertation mentions anthropologist David Miller and his work on materiality. Miller has written on the subject of clothing as material culture. Do you see your own interest in clothing as part of a broader anthropological perspective?

Jack Carlson:

Like most archaeologists, I watched too much Indiana Jones as a kid. But archaeology is essentially the study of material culture — the study of things — and I’ve always been interested in things: material objects and their meanings in terms of status, power, culture, and belonging. This includes clothing, of course. I’m interested in the ways humans choose to dress and adorn themselves — and why. Some of it has to do with what you might call practical considerations: the physical properties of certain cloths or materials; or the ways in which a garment is cut or constructed. But even more has to do with the cultural and social connotations of particular materials and garments. And this is true of what we call “Ivy style” or the “Ivy League look.”

I think my background in archaeology has made me particularly attuned to — some might say obsessed with — small details. It’s also made me very big on reading and research. After all, 70% of archaeology is done in the library (and “X” never, ever marks the spot!).

I’ll also add that I loved my time at Oxford. It helped to inform my sense of style and helped to deepen my understanding of menswear. So much of “Ivy style” traces its origins back to Oxford and Cambridge, and British boarding schools, and the clothes historically worn in those places for sport and leisure.

Matthew Longcore:

I read that Ralph Lauren discovered you through a pre-publication copy of your book Rowing Blazers and that he hosted a series of launch parties to promote the project. This served as your entrée into the apparel industry and inspired you to launch your own brand, also named Rowing Blazers.

Since then you have often been compared to Ralph Lauren. Do you admire Mr. Lauren and do you see yourself as following in his footsteps?

Jack Carlson:

I was out on a bike ride around Oxford one day, and felt my phone vibrating. I pulled over and looked at the phone: it said the incoming call was from “Ralph Lauren.” I thought it must have been about an online order or something, but I didn’t remember placing one. I answered, and I found myself speaking with Jerry Lauren — Ralph’s brother and the head of menswear at RL. My publisher had sent a pre-publication copy of my book to the RL office, and it ended up on his desk. He told me he loved the book and that he had shown it to his brother Ralph, and he loved it too. He invited me to New York to meet with them, and that’s how that partnership was born. They were so supportive and thoughtful. That’s what led to the launch of the Rowing Blazers book and ultimately the Rowing Blazers brand.

It’s funny being at J. Press now. I think as a business, RL is very different from what we’re doing at J. Press — though in many ways, J. Press is an important antecedent for Ralph Lauren. J. Press is the great granddaddy. The original Ivy brands like J. Press created the vernacular that younger, (much larger, more mainstream) brands like Ralph Lauren popularized later in the 20th century.

I have tremendous admiration for – and draw great inspiration from – Mr. Lauren and his company. I think Ralph Lauren both as a brand and as a person has been instrumental in keeping this style of clothing, “Ivy style,” in the mainstream. At the same time, Ralph Lauren is so big that it’s really its own genre at this point — and it goes well beyond Ivy: it’s the American west, it’s Jamaica, it’s the workwear world of RRL etc.

I’m so grateful to Ralph Lauren for all he has done for me, for the industry, and for American style.

Matthew Longcore:

The Financial Times (September 8, 2025) called you “the king of preppy.” What do you think of that title? When it comes to clothing and style, what do the terms “preppy” and “ivy” mean to you? Where does J. Press fit in?

Jack Carlson:

Ha — I often try to avoid the word “preppy” actually, because it means so many different things to different people. What I think about with that word, mostly, is The Official Preppy Handbook. My mom gave me her copy when I was in high school. Growing up, I dressed pretty “preppy,” if I can use the term, although for most of that time it wasn’t necessarily the cool thing. When I went to school in England as a kid, I had to wear a uniform everyday — complete with a little wool cricket cap and everything. And I used to keep it on all evening after school just because I liked wearing a blazer and tie. Back in the U.S., I wore hand-me-down Lacoste polo shirts, cricket sweaters, and old yacht club sweaters from my parents, and rugby shirts I had picked up during family trips around England, Ireland, France, and Italy — while virtually all of my classmates were wearing head-to-toe Y2K era Abercrombie.

Then a funny thing happened my senior year of high school: a brand called Ralph Lauren Rugby launched. And, at least in my corner of New England, that became the new cool thing. And suddenly everyone was dressing like me! But that was how I had been dressing the whole time.

“Ivy,” if you make the distinction, is much older, subtler. More academic, more tweedy. To introduce another modern-day term I despise, it’s more “old money.” And J. Press is quintessential Ivy.

But like Supreme Court Justice Potter Stewart said of pornography, “I shall not today attempt further to define the kinds of material I understand to be embraced within that shorthand description, and perhaps I could never succeed in intelligibly doing so. But I know it when I see it!”

Matthew Longcore:

The Official Preppy Handbook references J. Press and describes its customers as “ultraconservatives of the Old Guard.” That book was published 45 years ago, so much has changed, but there is still a sense that J. Press is one of the last vestiges of traditional menswear in America. How can J. Press attract a new generation of customers while at the same time retaining its traditional constituency?

Jack Carlson:

I love it. Nowadays, we hear the word “conservative” and probably think politics, though of course that’s not what Lisa Birnbach meant when she wrote. I think in some ways her sentiment is truer than ever. As many of the other old American men’s brands have turned in different directions, changed hands, or gone bankrupt in the last several decades, J. Press is, more than ever, the last bastion of real Ivy style and classic American menswear.

I plan to embrace that, and to make J. Press, more than ever, the standard bearer for Ivy style. I grew up with J. Press, shopping at the Harvard Square location — so a lot of the J. Press staples are almost sacred to me.

I’m also an academic: I’ve spent large chunks of my adult life reading and researching, especially when I was a doctoral student at Oxford — so I am a great believer in rigor, research, and authenticity.

I think all of that is actually the key to attracting a new generation. Thoughtful people with good taste like and appreciate authenticity, regardless of their age. So really,  I think the key is in not dumbing it down. Not trying to give it a more “mass” appeal. I think these are moves that some of J. Press’ historic competitors have made over the years, and I don’t think it’s worked out particularly well for many of them.

Made-in-America, Made-in-Scotland, Made-in-England: these are aspects of the brand that are extremely important to me. So is classic Ivy styling, and so are all of the classic Ivy details.

When my appointment was announced, I found it funny to read what some of the armchair pundits were speculating about what I’m going to do at J. Press — suggesting that I’m going to make it “zany,” or I’m going to water it down. A few people seemed to think I would just recreate the Rowing Blazers brand all over again, having sold it two years ago. I saw someone speculate that I was going to move our Shaggy Dog sweater production out of Scotland and change it to a polyester blend! Whoever these people are, they clearly don’t know me at all.

I’m not a one-trick pony. And a few items at the top of my list when I joined J. Press included: bringing back our focus on products made in America, Britain, Canada, Ireland, Norway, etc.; launching a creators series to highlight the people, places, and processes behind our most important categories; bringing back the Ivy-purist blazer, with the patch chest pocket, which J. Press, to my surprise, had not run for some time before I arrived; restoring the original color length and collar roll on our O.C.B.D. shirts, which is underway now; a renewed focus on the flap-and-patch Oxford shirt, for which J. Press has historically been known; restoring the historic white-and-red, slightly wonky, J. Press woven label; and all sorts of other small changes to bring the brand back into line with its heritage and pedigree, like grosgrain lapels rather than satin on our formalwear.

This is just the beginning, and not all of these changes can happen overnight. And, of course, there’s a lot of product that was developed and ordered before I arrived that we are selling now; and a lot of things I’m working on developing that are not ready yet.

But, from my perspective anyway, these are all changes that take J. Press back to its rightful place in the Ivy pantheon — rather than taking it to some new, uncharted place.

If you looked at the product assortment, the styling of the campaigns, etc., before I arrived, you would have seen a brand that was not fully embracing its core ethos in my view. You would have seen some product that was more Italian-leaning, or more generic-contemporary. Some of it sold well, but to me that is not the point if it does not connect directly back to the things that make us J. Press. So I’ve worked to phase out things that take J. Press away from what the brand is all about. And before I joined, you would have seen some styling choices which, at least from my perspective, did not have much to do with classic Ivy style. I’ve tried to change that too.

Maybe that makes me a reactionary — an “ultraconservative of the Old Guard” in Lisa Birnbach’s words. So be it. I’ll take it!

That’s not to say we can’t have fun. And part of me, perhaps, even likes getting a rise out of those who are determined to flip out. I introduced a version of the Shaggy Dog sweater with a little shaggy dog face (the one from the original label, which we’ve also brought back) as a Lacoste crocodile-style patch on the left chest. Not instead of the classic, patch-less, Shaggy Dogs. But in addition. And a couple people had full-blown meltdowns. Their minds could not comprehend. Or, at least, they pretended that their minds couldn’t comprehend. But that smiling little Shaggy face has proven extremely popular — and to me, they don’t take anything away from regular, plain Shaggy Dog sweaters! I own and wear both.

We can also have fun with a few unexpected collaborations or editorial pieces. That’s part of the job, and part of what I enjoy about it. But in my view, 90% of the business should be the core classics. And that’s where 90% of my energy is going — into making sure that we are doing those core classics better, and more consistently, than ever, and with all the correct details. I think that’s the real key to attracting new customers and doing the very best for existing customers.

Matthew Longcore:

The Ivy League look has been described as distinctly American, and yet we hear so many references to its English roots. How indebted is Ivy League style to England, and to what degree is the style truly all-American? How much of the current offerings from J. Press are made in the U.S.A.?

Jack Carlson:

I’m proud to say that the majority of J. Press’ offerings are made in the U.S.A. And of the rest, the vast majority are made in the U.K. and Canada. We don’t aim or purport to be a brand that makes every single item in every collection in the one given place. But I’ll go out on a limb and say that I don’t think there’s any other American menswear brand of J. Press’ size and scale making such a large percentage of its offerings in the United States. And that’s a great point of pride for me.

Our Austrian jacket is made in Austria; our Norwegian sweaters are made in Norway; our madras is from India; and our Aran sweaters are from Ireland, and so on.

Forty years ago or more, there were other brands alongside J. Press operating the same way. But today, in many ways, we are the last brand standing. I feel and bear the burden every day of keeping these factories going, and keeping the men and women who work in them employed. And, ideally, helping these factories to scale up and improve their operations. It’s a big responsibility, and it’s also an exciting opportunity. Everyone who shops at J. Press is part of this project too.

I love meeting the people behind our products. On my second day at J. Press, I met a gentleman who has been making ties for J. Press for over fifty years. He’s a Holocaust survivor who came to the U.S. as a teenager. He was in Auschwitz during the war. He’s in his mid-nineties, and he still comes to the factory almost every day. People and stories like this are part of why J. Press is such a special brand and place to work.

To answer your question about England — What we think of as Ivy style owes a huge debt to England. So much of it comes from the leisure and sporting attire traditionally worn at Oxford, Cambridge, and the great British boarding schools. That’s a big part of my world and my life personally, having grown up in England as a little kid and having gone to graduate school in the U.K. I think it informs my perspective on all of this, and on what I’m doing at J. Press.

And I think we can do more in that vein. When I arrived, we had button-down collar shirts and point-collar shirts in our ready-to-wear collection. But we didn’t have too many of what I would call proper dress shirts. English-style shirts, with a spread collar. And I know we can make them. We can make them in America, and we can make them really beautifully. With that swelled seam on the collar, etc. Some might think of it as being a little more British, but I think it has a place in our world.

Matthew Longcore:

J. Press is still considered a menswear brand. However, some of the models in the latest collection like Yale senior Imogen Cabot are women. Are you planning an upcoming launch of a women’s line from J. Press?

Jack Carlson:

I play with the idea. Not the idea of doing a full-blown women’s collection, but instead taking our core items and making women’s versions and fits. The exact same quality, make, etc., but for women: American-made Oxford shirts, blazers, khakis; Made-in-Scotland Shaggy Dog sweaters, and so on. Just really good, classic pieces in women’s fits. The demand is there; I hear it everyday.