Jack Carlson is menswear's archaeologist-in-chief

Jack Carlson says he would be a historian if he wasn’t designing clothes. The good thing about his role at J. Press is that he gets to do both. This is a company that is ‘born back ceaselessly into the past,’ to pinch a quote from F. Scott Fitzgerald, who almost certainly sported its blazers. J. Press will turn 125 next year, and there are few brands whose rich history is so vividly represented in the present. A time-travelling Yale man from the 1950s would feel instantly at home if his wormhole dropped him into the New Haven store — the Oxford button-downs, the sack suits, the ‘Shaggy Dog’ sweaters, the striped ties. The wider world, he would soon find, is rarely quite so reassuring.

But having a rich history is different from being stuck in the past. What’s engaging about the modern J. Press — Jack has been at its helm since summer last year — is how frequently and playfully it tries on new things. At Rowing Blazers, Jack’s previous company, which he sold in 2024, he was known for unexpected collaborations and eclectic references — Barbour to Babar the elephant. That same eye is at work here.

Jack has deep pools to draw from. He has a PhD in archeology. He is a collector extraordinaire (he has literally thousands of ties, to take one example) with the slightly faraway stare of a man who knows he is a long way down the rabbit-hole. J. Press’s archives are formidable, too. But even richer is the byzantine history of menswear over the past century or so since J. Press has been at large. Entire libraries could be written on the preppy-Ivy nexus alone. Several volumes might be dedicated to what is sometimes called ‘Ametora’, the Japanese take on classic American East Coast style. But perhaps it is Take Ivy that has become the canonical text — the landmark 1965 photo book by four Japanese entusiasts (Teruyoshi Hayashida, Shosuke Ishizu, Kurosu Toshiyuki, Hajime Hasegawa), which captured candid shots of life and style at America’s Ivy League campuses. Jack has just re-printed a handsome special edition of the book, and conjured a capsule collection around it. And so we started there.

JB: Tell me about Take Ivy.

The reality about Take Ivy is that it was this passion project of these three Japanese guys in the 1960s. Nowadays, the menswear nerd community thinks of it as this famous, ultra-important, central bible. But it was actually a very underground, very niche document for a long, long time. And the real Ivy movement in Japan that the book relates to very directly was actually a relatively short-lived phenomenon in Tokyo. It was almost like a punk movement.

The book was rediscovered about 15 years ago. Michael Williams started putting scans of it on his blog, back at the peak of menswear tumblrs. That enabled the images to disseminate very quickly. Now you see the same five scans from the book over and over again. But there’s a lot more to it than that. The writing, for one thing, is very cheeky. It’s very witty. It’s very funny. There’s a whole section of the book about J. Press as well. It’s a richer document than people understand.

JB: This is the archaeologist in you coming out. You have this rich library of references which you just can pull on at different times…

JC: Too many to even keep straight in my head. And I just try to keep running lists of projects that I want to do and try to keep them coming down the pipeline, basically. Last night we launched a collaboration between J. Press and Only New York. I look at them as the original when it comes to these downtown, graphic driven, streetwear-adjacent brands. They’re perhaps the original from which all these other brands — like Noah, Aime Leon Dore, and Kith — have kind of grown.

It’s just such great nostalgia. The graphics remind me of all the T-shirts that I would wear as a kid growing up. And both J. Press and Only New York have such deep roots in this city.

JB: You were known at Rowing Blazers for very playful, often unexpected collaborations…

JC: When I was starting Rowing Blazers, people thought of these collaborations as much more the domain of true streetwear brands, like Supreme and Palace. But from very early on, that was part of what I want to do. And I remember sitting with my co-founder, David, and we wrote down ideas for brands we wanted to collaborate with: Seiko, Barbour, Hunter, etc.

It’s one of the weirdest things — just how many of those actually ended up happening. But usually, the types of collaboration partners that I was approaching were individuals, artists, or from outside of the world of apparel. Harry’s bar, for instance, or Joe’s Pizza or Luke Edward Hall. And then the Targets and the Guccis and the Barbours — those were all inbound.

At J. Press, we have the history, the legitimacy, the legacy of the brand. And also, we can just do things that a lot of brands can’t do: like making stuff in the US, making our tailored clothing in the US. But I think the criteria for whom you collaborate with — it’s not a science, it’s an art. You’ve got to kind of feel it. To me, it’s got to resonate. There’s a reason to do it. It should paint out some corner of the picture of the brand that maybe hasn’t been painted yet.

JB: What do you think you’d be doing if you weren’t doing this?

JC: My original plan when I sold Rowing Blazers was to move to California and write. I have a big backlog of book concepts that I want to do. I’m still doing that. But it’s just at a much slower pace because I’ve got a lot to do at J. Press. I’m doing the Rugby Shirt book, but there are a lot of other book projects that I want to do as well. Some are coffee table books. Some are much more serious. I still want to turn my PhD thesis into a book, for example.

I’ve always kind of flirted with the idea of being in academia in some way. I don’t know that I want to do that as my entire thing, but I like the idea of being an adjunct or somehow being on the faculty somewhere and being able to write on the side.

JB: What was your PhD thesis about?

JC: I did archaeology. And the thesis is essentially about images of power in the Roman Empire and in the early Chinese Empire — the Qin and Han Dynasty. It’s a comparative study. And I think in some ways it’s still very relevant today. I think about this a lot.

If I had time, I would be writing much more about the ways that the Trump administration is using images and using social media. We see all sorts of things now that echo power in Rome. Trump is going to start putting his face on the coinage. His face is everywhere in Washington DC. The Kennedy Center is now the Trump Kennedy Center. And there’s something very Roman about what he’s doing to associate himself with Kennedy. There’s even talk of adding Trump to Mount Rushmore.

There’s something very Roman about all of this. You look at Roman relief sculptures of fictionalized versions of the emperor, who might be a decrepit old man, but is depicted as having a rippling six pack and stomping on his tiny pathetic enemies. And the Trump administration kind of does the same thing.

JB: That’s fascinating.

But the other thing, since we’re talking about this… I don’t know if you’ve seen this, but on Instagram, I get fed these reels just incessantly that are all about these fake guys who are about my age. These people don’t exist. But these profiles are all of these fake former Georgetown or Yale or Princeton lacrosse players. They all went to Exeter or Andover or Deerfield or Groton. Have you seen these guys?

JB: No…

JC: There are millions of them. When I first started noticing it, I was like, okay, someone’s done this sort of funny account. The bio is always something like: ‘Greenwich, Nantucket, Palm Beach, Deerfield class of ‘04, Cornell class of ‘08, Natty Champions, Lacrosse, Pledge Master.’ It’s an insane world to dive into, but it’s so prolific. It can’t just be made by AI. It can’t just be one person behind it. It’s like this whole crazy movement…

JB: Do you think they’re catfishing accounts? Or used for fraud?

JC: No — there’s something really strange going on with all of this. A lot of it is about Nantucket, a lot of it is about cocaine. There’s a sort of set of specific repeated references. Some are really MAGA. But some are really anti-MAGA — they’re really pro Democrat, pro Biden. And so then you’ll see they have beef with each other sometimes.

JB: This is so bizarre.

JC: And the accounts are even kind of consistent amongst themselves. They always have a first name and then, in quotation marks, a jokey middle name, and then last name, then they have their schools. Like this: ‘Stanwick “Peter Millar” DuPont; St. George’s 2007, Trinity lacrosse 2011, nose candy connoisseur, Harlem lacrosse coach, partner at Goldman Sachs.’

JB: So what could that possibly be for, for entertainment? For promotion/? They’ve got a couple hundred followers each…

JC: Some of them have a dozen followers. But some of them have 30,000 followers. Some of them have 101 followers — but then their video has 8 million views or something. It’s just absolutely insane. There is an entire parallel universe of fake people who all played lacrosse at these prep schools and East Coast colleges, apparently. It’s so strange. So I might do something with that. Maybe a podcast with an investigative element. How far does this all go?!

JB: We are in the midst of another bout of Kennedy intrigue. The Kennedys remain a big touchstone of East Coast and Ivy style. What do you make of that family’s enduring style legacy?

JC: We know today that the pretty pictures of Camelot came with a lot going on behind the scenes that wasn’t talked about. But JFK, without a doubt, was one of the most stylish presidents, maybe the most stylish of all time. I think Bush Senior had great style too, but he didn’t have the dashing good looks of Kennedy as a young man.

JFK was a J. Press customer, and he features heavily on my mood board. But it’s funny. As much as he’s an avatar of Ivy style, he did a lot of things that weren’t canonical. He didn’t follow all the rules. He famously liked two-button jackets instead of three-button jackets, and he would button both buttons, which is almost sacrilege. So now, whenever we post a mood board carousel and there’s a picture of JFK, you get all these angry teens obsessed with Ivy messageboards screaming: “But he has two buttons buttoned!” People lose their minds — even with JFK.