The last RollieFest in 2019 was somewhat of a seminal moment for me in my passion for vintage watches, and I didn’t even attend. Like many of you, I lived vicariously through Hodinkee’s photo report and marveled at all the wild watches on the wrists (and spread on the table) at this mysterious gathering.
The driving force behind RollieFest is Geoff Hess, now Head of Watches for the Americas at Sotheby’s, who organizes the gathering with the help of a number of industry friends. Sotheby’s was a partner for RollieFest 2023, but the event was funded largely by the tickets purchased by attendees invited to the event. Hess’ speech at the opening gala was a testament to his passion for collecting and his love and support of the community.
“The journey of watch collecting has been a cornerstone of joy for me throughout most of my life,” Hess said. “And for many years, along this journey, I think I often measured success in watch collecting by the specific watches I had, by the specific references I owned. The truth is, we all have a tendency to occasionally measure our success in comparison to our peers. Once in a while, we certainly compare our collections to those of others. But not tonight.”
“Tonight we are all equal. Tonight, we are all the same. Together, we all share the same passion. And together, we all share the same joy in simply sharing that passion with our friends.”
The weekend started off with a private gala at the American Museum of Natural History across the street from Central Park in Manhattan. Guests were reminded not to post pictures until the conclusion of the event to protect the safety and security of all the attendees and their valuable watches, security that was in part provided by Sotheby’s own team. Under the famous blue whale, collectors and enthusiasts dined, caught up with friends from around the world, and took a moment to grab some photos of rare Rolex watches in the dimly lit room.
That gala was just a taste. The next day, the crowd gathered for the RollieFest 2023 “Real Estate Conference” at the Rainbow Room, another hilarious way of disguising the remarkable nature of all the rare watches gathered in one place. And it wasn’t just Rolex that came out of collectors’ safes. With tables arranged on the sometimes-rotating central dance floor of the Rainbow Room, people spread out their watches, snapped wrist shots, shared stories about their finds, and discussed scholarship. A panel discussion – featuring Talking Watches alums Greg Selch and Fred Savage, among others – talked topics from the future of collecting to the economy to watch restoration.
Throughout the weekend, which finished with a cocktail hour at Manhattan Motorcars, watches also traded hands – whether for a few minutes or in longer-term deals – and sure, if you had a few hundred thousand dollars (okay, sometimes less), you could maybe pick up a watch or two on the table. But it seemed like the real joy for most collectors was getting a chance to catch up with old friends and, like any good watch lover, see some awesome watches.
I certainly couldn’t capture all the watches – in fact, some only came out of their cases for a few minutes – but I did my best. With that in mind, it’s my pleasure to bring you inside one of the wildest collector gatherings in the world.
Day 1: A Night at the Museum
Day 2: A Foggy Morning at the Rainbow Room
Security looked tough with this great G-Shock. He also seemed utterly confused at why I’d ask to take a photo.
Tiffany. That’s all.
Day 2 Evening: Cars and Cocktails
