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RollieFest 2023: Celebrating Vintage Rolex Watches and Timeless Connections

In a world where time never stands still, there exists a place that defies the relentless march of progress. It's a gathering known as RollieFest, where vintage Rolex watches take the spotlight, but the true stars are the enthusiasts who share an unwavering love for these horological treasures. Join us on a journey through RollieFest 2023, where we'll explore an event that has evolved alongside the ever-changing world and the vintage Rolex collecting community.

RollieFest isn’t just an event; it’s an honor, an opportunity extended to only the world’s foremost collectors and dealers. Beyond the chance to witness some of the planet’s most coveted vintage Rolex watches up close, it’s a nexus of passionate souls, a place where friendships and shared fervor unite individuals from every corner of the globe.

"RollieFest: Where Vintage Rolex Enthusiasts Unite for an Unforgettable Experience!"

The last time I was at RollieFest, the world was entirely different. Not to mention, the vintage Rolex collecting community as a whole was also different. To be included and invited to this event is an honor, as only the world’s top collectors and dealers are invited to attend this event. This event is much more than just a prestigious opportunity to see, explore, and handle some of the world’s best and most sought-after vintage Rolex watches. It is also an event that connects me to some of my closest friends and peers who share the same passion as me worldwide!

Every detail Rolliefest is thoughtfully and thoroughly considered, from the event’s name tags and entry badges to the umbrellas and event merchandise. Geoff Hess @manhattanrollie, who I call a personal friend and whom I have gotten to know closely over the years, sits at the top of the key, also having just taken the head position at Sotheby’s after leaving Phillips watches. Geoff is a true collector, and his passion for vintage Rolex can be seen at every intersection of this event. 

The event for me started a few days prior as friends, peers, and volumes all descended into NYC to attend the event. Just having returned from 3 weeks in Asia, as you may have seen from our social media accounts, there is no rest in the vintage watch world for us here at Craft + Tailored, even though we arrived in NYC a few days before the event to catch up with clients and our connections here in NYC we hit the ground running.

RollieFest 2023 Day #1

RollieFest starts with a Gala Dinner and this years opening event was held at the American Museum of Natural History next to  Central Park in Manhattan. Under the great blue whale, surrounded by 117 of the world’s top collectors from 17 different countries, Jeff Hess greeted the attendees and, while dinner was being served, during his address to the elite-level attendees said “People always ask me how I got started in watch collecting, but no one asks me where it has led me” this is something that resonated with me deeply as this past year I flew over 400k miles visited countless countries and met with clients and peers new and old. This statement was heartfelt and struck close to home for me as this watch obsession and passion has brought me to places near and far and has truest become my life’s work. At the dinner, watches began to make their appearances, with more than one attendee ‘double wristing.’ However, the primary emphasis was on reconnecting with old friends and setting the stage for the upcoming day, during which all the watches would be showcased.

RollieFest Day # 2 A Rain Engulfed Rainbow Room

The day two luncheon is the main event of RollieFest. All the watches come out, and this is where the real magic of RollieFest happens. This year’s event was on the 65th floor of Rockefeller Center’s Rainbow Room. Entering the room, my hands tingled with excitement as the event was about to start. Watches immediately begin to come out of bags, cases, and rolls, all proudly displayed on large and long tables in the center of the spinning floor of the Rainbow Room.

Grail heaven, Rolex Milsubs, Daytonas, gemset Day-Dates, perpetual calendar moonphase’s, tropical this and tropical that, big crown subs, sure, why not a handful? The words vintage Rolex collector elite lay them all out on the tables proudly to share and to discuss. The views from the Rainbow room on the 65th floor are excellent, but the weather didn’t allow much of a view of the city below. But in reality, many attendees would not have bothered to look out the window as the main focus and view was in the center of the room, and all eyes and hands were swarming over what lay before everyone.

During the lunch, a panel discussion occurred where Geoff Hess and a panel of collectors and industry insiders like Bulang and Sons Bernhard Bulang and Leigh Safar Vice President Specialist in the Watches Department at Sotheby’s, discussed how the market has changed and evolved since the last RollieFest which occurred in 2019 other panelists included celebrity’s like Fred Savage and watch enthusiast Morgan King discussed what watch collecting meant to them and how their passions have evolved and changed over the years.

RolleFest 2023 Event Recap

As I reflect on my time at RollieFest 2023, I can’t help but appreciate how this event transcends the boundaries of collecting watches. Our company saying here at Craft + Tailored is, “It’s more than just watches,” and RollieFest reflects this statement. RollieFest is not just about the watches; it’s about the connections forged with like-minded individuals from around the world who share a deep and abiding passion for vintage timepieces. RollieFest is a celebration of the past, present, and future of watch collecting, and it’s an honor to be a part of this incredible community.

In a world that’s constantly changing, Rollie Fest remains even since having attended the event in 2019 when the world was quite a different place altogether RollieFest remains a timeless gathering of enthusiasts bound by a shared love for vintage watches. As I left the Rainbow Room, I couldn’t help but wonder where this obsession would take me next, for in the world of vintage Rolex collecting, the journey is just as extraordinary as the timepieces themselves.

Special Thanks

A special appreciation goes out to Geoff Hess and his exceptional team. They not only extended an invitation to me and my Craft + Tailored co-pilot, Tyler Vanes, for this event but have also been staunch supporters of the Craft + Tailored brand. Collectors and individuals like Geoff, who share the same fervor for collecting as we do here at Craft + Tailored, are invaluable. I am deeply honored to call Geoff a personal friend.

I am genuinely excited for Geoff, who has recently assumed the role of Head of Watches for the Americas at Sotheby’s. With the vintage watch auction market having faced its fair share of challenges in recent years, I believe change is overdue. In my opinion, Geoff, alongside his formidable team, which includes Skip Powell formerly of SAGA Trading Co., Leigh Safar, and Rich Lopez, represents the positive change that the auction environment has needed for quite some time.

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