J. Press aims for sweet spot between prep and Ivy
Jack Carlson’s first collection for J. Press blends classic Ivy staples with loud colors and go-to-hell styling. Can it draw a general audience without alienating trad purists?
NEW YORK — J. Press’ Fall/Winter 2025 debut saw the brand attempt to fuse Ivy’s quiet traditionalism with prep’s loud irreverance. Presented Thursday at the Explorer’s Club in Lenox Hill, Manhattan, the collection signaled its new leadership’s strategy to court a broader audience while holding onto the brand’s loyalist core.
In the weeks leading up to the show, academic and menswear entrepreneur Jack Carlson — a former U.S. national team rower and founder of Rowing Blazers — told the Financial Times’ Robert Armstrong he aims to restore Press’ position as a “standard bearer for American menswear and Ivy style,” after being named creative director and president of the New Haven–founded collegiate outfitter in September.
Drawing on the maximally preppy style he developed at Rowing Blazers, Carlson’s first collection is more suited to an East-Coast campus than a corporate boardroom. Carlson appears to be wagering that fun, approachable preppy stepping-stones can bring a younger, less niche crowd into the J. Press fold. New eye-poppingly bright Shaggy Dogs or mufflers styled in jaunty ways can act as style entry points, luring Ivy-curious newcomers toward the classic tailoring, shirts and accessories that keep its trad, loyalist core coming back.
Menswear influencer Simon Goldman thinks Carlson’s strategy could work.
“Some of those out-there pieces might really resonate and bring new people in that will then hopefully find some of the beautiful sack suits and other staples J. Press is known for,” Goldman said after the runway show. “The show leaned into the styling, which felt very new and exciting for J. Press.”
J. Press has historically represented a careful, highbrow ethos: the brand has long been marketed toward discerning men who appreciate exceptional quality and the subtle markers of the Ivy style tradition. It has only rarely chased trends, largely prioritizing classic tailoring, Oxford shirts and accessories.
Today Carlson is explicitly courting a new generation, tapping social media influencers, fashion week spectacles and over-the-top pieces designed more to build brand lore than for daily wear. An umbrella with panels made from vintage Ivy League pennants, hunt ball–inspired tailcoats and a patch-covered navy blazer are just a few examples.
Some of these more modernist, Rowing Blazers–inspired elements of the collection have sparked concern among menswear aficionados that contemporary pieces might overshadow the classics J. Press is known for. Prominent logos on rugby shirts and reverse-weave crewnecks, slogan’d sweaters, clashing colors and emblems on Shaggy Dogs have fueled debates in Reddit menswear circles and at New York men’s fashion events about whether J. Press even needs a refresh. Its stodgy reputation is after all, for many Ivy clotheshorses, the whole point.
“Some of these outfits are heavily leaning into the Rowing Blazers vibe of bright clashing colors,” a top comment on the r/NavyBlazer Reddit discussion thread wrote. “[I’m] more of a fan of their more traditional outfits. I respect Mr. Carlson as a business person but I hope he doesn’t ruin what has led the J. Press brand to endure for this long.”
Goldman said despite Carlson’s go-to-hell take on Ivy, most of the collection tracks closely with Press’ historic offerings.
“They kept a lot of the pieces quite classic and traditional to where I could walk into J. Press and it wouldn't stand out or feel out of place,” Goldman said. “The styling is what kind of brought it to like a newer, younger generation with punchy colored socks, some really fun new colors of Shaggy Dog sweaters draped in creative ways, aggressive stripes and then there was also some more conceptual kind of very Rowing Blazers influenced new pieces, like the logo’d up sweaters, the blazer with patches all over”
Longtime Ivy enthusiasts see Carlson’s arrival at J. Press as an opportunity to return the brand to its best era. A commenter on Ivy Style, following Carlson’s announced hiring, characterized the moment as an opportunity to reinvigorate the brand. He petitioned the new leadership to focus in specifically on what he says was Press’ golden era, roughly from the mid-fifties to the late sixties.
“I’ll concede this is an opportunity: to work with makers to create models and fabrics that are unique to J. Press…; to revive and refresh old, time-tested patterns and cloth circa 1950s and 60s; to do away with the cheap, kitschy (and overpriced) logo-saturated stuff and focus on high quality inventory,” the commenter noted. “The charm of this style is how the traditionalist old-fashionedness merges effortlessly-and-organically with collegiate sportiness…those [golden era] brochures affirm the superb taste of the Press brothers — and confirm what we’ve known for a while: both the inventory and the branding have been less than what they could be — for a good, long while now.”
Even for Ivy purists — like the readers and writers that contribute to this blog — it can help to take a step back and view J. Press from a broader perspective. The brand may be able to “walk and chew gum”: maintain and improve its Ivy core that underpins its cultural cachet, while also taking risks that can expand its appeal. As one Reddit commenter noted, for J. Press to improve its reach, it has to meet customers where they are.
“Reality check: Sack suits went out of style like 60 years ago, your average bloke on the street doesn't wear tweed jackets and almost no one even knows what an ‘OCBD’ is unless they're already #menswear-pilled,” the commenter wrote. “Most people who frequent communities like this aren't really in a good position to determine what the general public wants to buy.”
Ivy and prep, while often spoken of in the same breath, are distinct but overlapping takes on classic American menswear. Ivy is about subtle elegance, quality and the quiet logic of proportion and texture. Typified by the boneless, or unstructured sack jacket, well-worn oxford shirts, khakis and understated polished shoes. Prep, a more playful cousin, leans into sporty markers of a historically aristocratic lifestyle , including polo shirts, critter prints, bright tartans and sharp contrast. Some observers even suggest that preppy is just what Ivy-style dressers wear in college, before they mature into trad jackets, slacks and loafers over time. Carlson’s first collection at J. Press sits at this intersection of the two.
As Jason Jules, author of Black Ivy and a J. Press runway model, noted after the show, Ivy has always threaded its way through American style trends.
“There's always a through line of Ivy in terms of any current trend, but they just change the name,” Jules said. “So one minute, it's old money, now it's preppy, next year, it'll probably be nautical or something, but it's always, you know, Ivy referenced.”
Centering statement pieces like patchwork wool sweaters, expansive muffler and Shaggy Dog colorways, striped and plaid “fun shirts,” and plaid duffel coats all seem to offer non Ivy-pilled “normies” a gateway into classic menswear, even if not willing to wear a jacket and tie, just yet.
Carlson’s challenge will be balancing two audiences under one roof: maintaining staples like repp ties, Oxford cloth button-downs, navy blazers and tweeds, while exploring more contemporary styles. Expanding the range of pant silhouettes to include high-rise pleated trousers reminiscent of 20th century Esquire illustrations would also be smart. Unbranded Shaggy Dog sweaters and rugby shirts should also remain so as not to alienate the core trad audience.
“When he left Rowing Blazers, I had a feeling that he'd be going somewhere interesting. So when I heard that he was here…it makes perfect sense,” Jules said. “He's done such a great job in terms of creating a brand from zero that I’m excited to see what he does with this heritage brand that needs some attention and kind of contemporary relevance.”
Lets see what he does. Personally I am not too enticed by super bright clashing colors mixed with classic Ivy style so let’s hope he has another gear. Getting back to proper proportions and correct fit for garments could draw many that are stranded on slim and low island if they can be educated on why they just work to improve what you have rather than take away.
Great piece. Excited to see it all unfolds for the brand, and Jack.