How a '90s Sailing Watch Beloved By JKF Jr. Became 2025's It Timepiece

‘90s prep—in all of its relaxed, rich, and studied nonchalance—is back. Boat shoes are everywhere. Rugby shirts have had a renaissance. And energized by images from Ryan Murphy’s upcoming American Love Story series on Carolyn Bessette-Kennedy and John F. Kennedy Jr., the internet commentariat can’t stop arguing about how to do the era’s signature style justice.

But for Brynn Wallner, founder of the massively popular luxury watch platform Dimepiece, reviving ‘90s prep in the ripe year of 2025 came down to pulling one specific piece out of the vault: the Timex Intrepid, a stainless steel sailing watch beloved by JFK Jr. during the decade—only this time, reworking it so women can wear the timepiece, too.

A pioneer within the women's watch collecting space, Wallner partnered with Alan Bedwell, a vintage watch dealer and founder of Foundwell, and the American watch brand to release the Timex Intrepid Dimepiece edition, launching today, August 7. “It’s a scaled-down, more femme-friendly version of the watch at 36mm (versus the 46mm of the original) that’s super easy to wear, regardless of gender and wrist size,” Wallner says over email. “It also feels very true to my personal style, which is inspired by '90s prep and the promise of New England—summers swimming in the ocean, tan skin, salty hair, taking long walks, getting invited on sailboats, blackberry soft serve, etc.”

Wallner reconnected with the Timex Intrepid on a deep dive of JFK Jr.’s image archive, coming across a photo of the late, legendary American attorney and publisher wearing the 1995 dive-inspired, water-resistant watch. She and Bedwell, who’ve worked together since 2021 curating watch collections for luxury retailer Dover Street Market and selling pieces to Charli XCX, Bad Bunny, and Debby Ryan, had an instinct that the piece would succeed as a modern-day revival. Not only because of the preppy landscape of 2025’s trends, but since the Timex Intrepid 1995 taps into the enduring appeal of John-John—“everyone seems to be cosplaying like they're part of the Kennedy family right now,” as Wallner puts it.

The duo reached out to Timex and proposed a rerelease of the Intrepid 1995, which took shape in a spring 2025 drop of the throwback style that sold out shortly after its initial release. “Timex’s reissued Intrepid 1995 also found its way onto the actor Paul Kelly in BTS shots of Ryan Murphy's American Love Story, a huge validation for us,” Wallner adds.

But Timex’s smaller-sized, quartz movement team-up with Dimepiece, Wallner’s first-ever watch design collaboration, is an achievement that represents far more than just the endurance of prepster style and Kennedy’s everlasting cool. It’s a step within the watch industry—a notoriously exclusive, slow-moving, and typically boys-only club—toward genuine inclusion.

“Somewhere around the Y2K era,” Wallner explains, “most watch brands halted production on their smaller sports watches, and watches marketed to women were stripped of their simplicity in favor of diamonds, pink dials, and other stereotypically girly attributes. My style is more gender-neutral with a borrowed-from-the-boys vibe, which I felt was missing from modern watch offerings. Of course, I love a slinky Cartier Panthère or a gem-set Chopard watch, but I was craving something sporty and gender neutral, yet cute—which is what this Timex is. It satisfies my desire for what I want to see more of in the industry.”

The Timex Intrepid x Dimepiece isn't a watch designed by a brand assuming what their women shoppers will want to wear; it’s a watch designed by a woman watch connoisseur who knows what pieces she, as well as countless other consumers, actually want on her wrist. The timepiece is available for $239 at timex.com now.