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    Home»Gear»Inside the Watch-Filled Fashion Show That Put Important Vintage Rolexes, Omegas, and More on Every Model
    Gear

    Inside the Watch-Filled Fashion Show That Put Important Vintage Rolexes, Omegas, and More on Every Model

    By September 12, 2025No Comments3 Mins Read
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    This is an edition of the newsletter Box + Papers, Cam Wolf’s weekly deep dive into the world of watches. Sign up here.


    J. Press’s new creative director, Jack Carlson, and Eric Wind, the famed watch dealer behind Wind Vintage, started out at Georgetown together in 2005. Looking for ways to rep his university’s colors, Wind strolled out to the school’s gift shop and picked out a grey-and-blue striped tie. Little did he know he committed a grave faux pas. Thankfully, Wind quickly established a friendship with Carlson and it wasn’t long before Carlson helped remedy his schlubby necktie situation and find a more fashionable alternative. “We were in our first month,” Wind tells me over the phone Wednesday morning, “and [Carlson] said, ‘We got to go get you the proper tie.’” That’s when the designer steered his new friend towards the DC location of legendary Ivy outfitter J. Press. “This is where you actually get the good stuff,” Wind remembers Carlson telling him. Now, Carlson (who founded the disruptive prep brand Rowing Blazers) is heading up Press—and watches are suddenly a big part of the picture.

    Take Carson’s first fashion show for J. Press. On Wednesday morning, less than 24 hours before it was set to kick off, the ground was still shifting between the designer and Wind’s feet as we chatted on the phone. Carlson planned for every model to wear a watch, but the number of guys who’d be walking down the runway suddenly jumped from 32 to 36. Wind Vintage’s VP and senior watch specialist Charlie Dunne was still on the plane transporting 32 watches (33 if you include the ‘50s-era Rolex Air-King on his wrist), from Florida to New York City at that very moment.

    A Tudor Submariner

    Greg Kessler/KesslerStudio

    “I would’ve thrown in some more watches,” Wind says.

    “Well, this is all happening in real time,” Carlson replies. “We’re doing castings and fittings right now.”

    A plan to incorporate Carlson’s own “Domino’s” Rolex—an Air-King stamped with the pizza chain’s logo on it—and a couple of his Seikos is quickly drafted to accommodate the extra wrists (the designer ended up wearing the Domino’s watch himself instead). The watches will fit nicely with the existing mix, a vibrant collage of vintage and modern pieces from Rolex, Bulova, Jaeger-LeCoultre, Tudor, and Omega that tell Wind and Carlson’s stories. The pieces were explicitly chosen for their personal significance, either to one or both of the partners, like a Jaeger-LeCoultre Reverso Carlson gave Wind on his wedding day.

    Fashion important model Omegas put Rolexes show Vintage WatchFilled
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