By Rifan Muazin 
The atmosphere backstage at a J.Press runway show is a meticulous blend of Ivy League tradition and high-fashion intensity. Before the Fall-Winter 2026 collection made its debut on Wednesday, designer Jack Carlson—the man tasked with steering one of America’s most storied heritage brands into the modern era—was seen personally inspecting every model. For Carlson, whose background with Rowing Blazers has always been rooted in the granular details of "preppy" subculture, the clothing is only half the story. He adjusted ties, fluffed the iconic "Shaggy Dog" sweaters, and ensured that bags were stuffed with just the right amount of weight to simulate a commuter’s hustle. However, the final check for every look was focused squarely on the wrist.
In a move that has become a hallmark of Carlson’s tenure at J.Press, the brand collaborated with Eric Wind of Wind Vintage to provide the horological soul of the show. Wind, a former Vice President at Christie’s and a legendary figure in the vintage watch world, flew in a curated collection of 50 museum-grade timepieces from his headquarters in Florida. These weren’t just props; they were individually bubble-wrapped treasures that represented over a century of watchmaking history. Escorting these pieces was Charlie Dunne, Wind Vintage’s senior watch specialist, who noted that while there is an aspirational "science" to pairing a watch with a blazer, sometimes the selection was driven by the models themselves. "Everyone wants a Rolex," Dunne remarked, reflecting the universal gravity of the "Crown." Yet, as the show proved, the world of vintage horology offers far more than just brand recognition—it offers a narrative of survival, utility, and timeless style.
The partnership between J.Press and Wind Vintage is a natural extension of the "Ivy Style" ethos. J.Press was founded in 1902 on the Yale University campus, and for over a century, it has been the definitive outfitter for the American academic and social elite. Watches have always been the silent partner to the navy blazer and the repp tie. In the mid-20th century, a watch was a graduation gift, a military companion, or a professional milestone. By bringing these specific vintage pieces to the runway, Carlson and Wind are not just accessorizing; they are contextualizing the clothes within a continuum of heritage.
Among the 50 pieces selected, 13 stood out as the definitive highlights of the Fall-Winter 2026 show. Each tells a story that resonates with the rugged, refined, and often eccentric world of J.Press.
1. The Tudor Oyster Prince "Navy Veteran"
The standout piece of the collection was a vintage Tudor Oyster Prince with a backstory that sounds like a watch collector’s fever dream. Originally owned by a member of the United States Navy, the watch had clearly seen the world. It was a "tool watch" in the truest sense, worn hard through years of service. When the veteran’s estate was being cleared out, the family nearly discarded the piece, assuming its battered exterior meant it was worthless. It was only when someone noticed the "Rolex" branding on the caseback—a common feature for Tudor pieces of that era, as Tudor utilized Rolex’s patented Oyster cases—that they realized its potential value.
After Wind Vintage acquired the piece, it was given an ultrasonic bath to remove decades of grime, but the integrity of the watch remained untouched. It features sharp, unpolished edges and a dial that screams authenticity. Seeing a watch that survived the rigors of the Navy find a second life under the bright lights of a New York fashion show is a testament to the durability of mechanical watchmaking. It perfectly mirrored the J.Press aesthetic: items that are built to last and look better with a bit of "honest wear."
2. Rolex Ladies’ “Domino’s” Datejust
One of the more whimsical yet highly collectible niches in the Rolex world is the "Domino’s" dial. Starting in the late 1970s, Domino’s Pizza founder Tom Monaghan began gifting Rolex watches to franchise managers who hit specific high-sales targets—originally $20,000 in a single week. While the most common variant is the Air-King, Wind brought an exceptionally rare ladies’ Datejust to the J.Press runway.
This two-tone piece is a rarity because, as the lore goes, once a franchise owner earned their own Rolex, they could eventually earn a second, smaller version for their wife. This specific watch belongs to Abigail Harris, Wind Vintage’s director of marketing and logistics. Its presence on the runway highlighted J.Press’s historic move this season: the introduction of its first-ever womenswear line. The Domino’s Rolex is the ultimate "if you know, you know" piece, blending corporate Americana with Swiss luxury in a way that feels inherently "preppy."
3. Abercrombie & Fitch by Heuer Seafarer
Before Abercrombie & Fitch became a mall staple defined by cologne-heavy showrooms, it was the world’s premier outfitter for hunters, fishers, and explorers. During the mid-20th century, A&F partnered with Heuer to create the Seafarer, a chronograph designed for the outdoorsman. The Seafarer features a unique tide complication, allowing the wearer to track high and low tides—a vital tool for the coastal elite of New England.
The version seen at the J.Press show was paired with a baby blue NATO strap, emphasizing the "Cape Cod" vibes of the collection. It is a reminder of a time when luxury was defined by utility and when Heuer was the undisputed king of specialized chronographs.
4. Rolex GMT-Master in Yellow Gold
If the "Pepsi" GMT-Master is the quintessential pilot’s watch, the solid gold version is its executive counterpart. However, the example on the runway subverted expectations. Lacking the traditional two-tone ceramic or bakelite bezel and stripped of its metal bracelet in favor of a rugged leather strap, this GMT-Master looked less like a status symbol and more like a cherished heirloom. It represented the "classic with a twist" philosophy that Jack Carlson has championed, proving that even the most prestigious watches can be dressed down for a more soulful look.
5. Universal Genève Polerouter
The Universal Genève Polerouter is currently experiencing a massive renaissance in the collector market, spurred by Breitling’s 2024 announcement that it would be reviving the dormant brand. The Polerouter was famously designed by a young Gérald Genta (who would go on to design the Royal Oak and Nautilus) to commemorate the polar flights of the Scandinavian Airlines System (SAS).
The example at J.Press featured the iconic crosshair dial and "Big U" logo. It is a masterclass in mid-century design, offering a level of sophistication that punchy modern watches often lack. Its presence on the runway served as a nod to the "insider" nature of current watch collecting.
6. Heuer Autavia “Jo Siffert”
While Steve McQueen made the Heuer Monaco a household name, serious racing enthusiasts have always gravitated toward the Autavia, specifically the "Jo Siffert" variant. Siffert, the legendary Swiss Formula One driver, was the first to wear this specific white-dialed chronograph with blue accents. The "C-shaped" case gives it a funky, 1970s silhouette that paired perfectly with J.Press’s more adventurous corduroy and tweed patterns.
7. Jaeger-LeCoultre Étrier
The Étrier (French for "stirrup") is a definitive piece of equestrian-inspired design. Given that equestrian sports are a pillar of the Ivy League lifestyle, this Jaeger-LeCoultre was a natural fit. Interestingly, the watch was styled across gender lines, reflecting the modern trend of women wearing "men’s" vintage and men embracing smaller, more rectangular "cocktail" styles. It is a piece that feels more like jewelry than a machine, highlighting JLC’s reputation as the "watchmaker’s watchmaker."
8. Gallet Multichron Decimal "Big Eyes"
Gallet is a brand for the true horological nerd. The Multichron Decimal, with its oversized subdials (hence the "Big Eyes" nickname), was designed for professionals who needed to measure time in decimal units. With its silver dial and sharp red accents, it provided a technical contrast to the soft textures of the J.Press knitwear.
9. Jaeger-LeCoultre Reverso
No vintage collection is complete without a Reverso. Originally designed for British Army officers in India who needed a watch that could survive the rigors of a polo match, the Reverso’s ability to flip its face over remains one of the greatest "gimmicks" in history. The example on the runway was a study in minimalism—two hands, a cream-colored dial, and an exquisite metal bracelet that caught the light with every movement of the model’s wrist.
10. Rolex GMT-Master “Pepsi”
The "Pepsi" GMT-Master is perhaps the most recognizable vintage Rolex in the world. With its red-and-blue bezel designed to distinguish day from night for Pan Am pilots, it is the ultimate travel watch. The example provided by Wind was a "dream" specimen, showing the perfect amount of bezel fading (often called "ghosting" by collectors) that only comes from decades of exposure to the sun.
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11. 1960s Dunhill
One of the most aesthetically pleasing pieces was a 1960s Dunhill with a deep blue dial and Breguet-style numerals. Dunhill watches from this era often utilized high-quality Swiss movements and focused heavily on the elegance of the dial furniture. This piece was a reminder that during the 60s, style was often found in the simplicity of a well-proportioned dress watch.
12. Charlie Dunne’s Personal Rolex Datejust “Wide Boy”
A personal touch was added with Charlie Dunne’s own Rolex Datejust, a "Wide Boy" variant characterized by unusually thick hour markers and hands. The watch features a sentimental engraving on the back: “To Chuckles ‘A Wide Boy For My Wide Boy’ Love Enrique.” The exchange of nicknames between Wind and Dunne adds a layer of human connection to these mechanical objects, reminding us that watches are often the vessels for our most important relationships.
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13. Rolex Bubbleback with California Dial
The final piece, though it didn’t make the official runway walk, was seen backstage on the wrist of a collector. The "Bubbleback" earned its name from the protruding caseback required to house Rolex’s early automatic movements. This specific example featured a "California Dial"—a quirky layout that uses Roman numerals on the top half and Arabic numerals on the bottom. It remains one of the most charming and enigmatic designs in the Rolex archive.
As the show concluded and the models returned the watches to their bubble-wrapped safety, the impact of the collaboration was clear. By integrating these 50 vintage pieces into the Fall-Winter 2026 collection, Jack Carlson and Eric Wind proved that "new" fashion is at its best when it is anchored by "old" soul. In the world of J.Press, a watch isn’t just a way to tell time; it’s a way to tell a story.
