The Best Vintage Watches From the J. Press NYFW Show

There’s a serious problem with fashion shows, according to Eric Wind: Not enough watches. As one of the world’s foremost vintage watch dealers, however, he recognizes that he might be somewhat biased. “Obviously, it’s mostly about the clothes, but it feels like they’re just naked when they’re walking out,” he says. “Even the Ralph Lauren show—there were no watches on the wrist. It’s like, ‘Where are the watches, man?”

Fortunately for anyone who shares this view [raises hand], there was one show at New York Fashion Week that gave timepieces their due. When Jack Carlson, president and chief creative officer of J. Press, presented his latest collection for the stalwart Ivy League outfitter, there was a vintage wristwatch to complement each look.

Carlson and Wind met during their freshman year at Georgetown, and in the two decades since, Carlson founded (and sold) Rowing Blazers—another paean to Ivy League style—while Wind became a go-to supplier of tropical dial Submariners and Paul Newman Daytonas to the world’s most discerning collectors. Having previously collab’d with the likes of Tudor, Seiko, and Zodiac on runs of special pieces for Rowing Blazers, the duo’s partnership opened a new chapter at NYFW last fall, when Carlson paired his debut collection for J. Press with a selection of watches from Wind Vintage. Just five months later, the story continues with the launch of the brand’s spring/summer collection and the relaunch of a classic menswear tome.

“The show is a tribute to Take Ivy, which is having a real moment right now,” explains Carlson, referencing the classic 1965 compendium of Ivy League style written by four Japanese menswear enthusiasts. “I began working on this concept as soon as I knew I was coming to J. Press,” says Carlson, who is releasing a special edition of Take Ivy in conjunction with the show. “J. Press features prominently in the book, with photos of the New Haven, New York, and Cambridge shops, so it felt like a natural foundation. The Ivy League look may be trending, but for J. Press, it isn’t a trend—it’s our heritage. The brand helped define Ivy style, and I wanted us to lean into that role as a standard-bearer for classic American menswear.”

Of course, this presents the perfect opportunity for an expert such as Wind to pick out a few—37, actually—of his favorite vintage watches from the Take Ivy era to accompany Carlson’s looks. “I think [for] every watch guy, when you watch a runway show, and there are no watches, it’s almost a little hard to watch,” he says. “And for fans of watches and vintage watches in particular, there is no show like the J. Press show.”

Indeed, there isn’t. Beneath the models’ Shaggy Dog sweaters and monogrammed cuffs, you’ll see plenty of two-tone Datejusts, old Subs, and even a few chunky Heuer chronographs, all of which also happen to be listed for sale at Wind Vintage. “For the watches, we focused on pieces that would feel authentic to that Ivy League context—understated, refined, and historically appropriate rather than flashy,” says Wind. “These are mostly vintage watches that a student, professor, or young professional in that era might realistically have worn. We selected pieces that complement the clothing rather than compete with it. The goal was cohesion: watches as part of the overall look, not accessories that draw attention away from the garments. Many are classic dress watches in modest sizes, with clean dials and leather straps.”

Today, it’s easy enough to look at watches like these—along with the repp ties and sack suits of the 1950s and ‘60s—as relics from another era, but Carlson and Wind don’t see them that way. While sweats and sneakers might be more prevalent on the campuses of Yale and Harvard today, the look associated with these august institutions of higher learning—including its watches—remains an important element of the American sartorial pantheon. “Ultimately, the show is about presenting Ivy style not as nostalgia but as something living and relevant,” says Carlson. “The clothes, the books, and the watches all work together to tell that story.”