A Watch Club That’s Different From the Others

Henry Flores, the founder of Classic Watch Club, grew up in East Harlem in a household where he was raised to appreciate well-made items.

“My family didn’t come from money but my mom loved good quality things,” Mr. Flores, 44, said over a pizza at a short walk from his childhood home. “She’d say, ‘If you buy something good, you’ll only have to buy it once.’”

Inspired in part by the two-tone Seiko that his father wore on special occasions until his death in 1992, Mr. Flores was in his early 20s when he began to be interested in watches. In 2004, he bought his first watch, a 39-millimeter 40th anniversary edition TAG Heuer Carrera, in a duty-free shop on St. Thomas, in the U.S. Virgin Islands, on his way home from a family trip.

His horological knowledge has expanded significantly since then. Initially, he said, he frequented online forums and horological websites such as Hodinkee. He gradually began meeting other collectors by attending local gatherings, too.

Over time his collection has grown to 14 watches, not including several MoonSwatches. The majority of them are vintage. (He’s posted photos of some of those timepieces on Instagram.)

He’s especially fond of what he described as “luxury sports watches,” like his two Omega Speedmasters and three Rolex Submariners (one by Tudor), because, as he put it, “They serve a purpose and you don’t have to be too delicate with them.”

His modern watches include two Audemars Piguet Royal Oaks, which he called “the pinnacle of the modern luxury sports watch.

In May 2019, he founded Classic Watch Club. “I figured, why not assemble a group of aficionados/experts that can help each other navigate the minefield of vintage watch collecting,” he said.

It meets twice monthly, once online and once in person, usually at a club for car aficionados in Midtown Manhattan. About 125 of its nearly 300 members live within driving distance of New York City; the others come from countries including England, the Netherlands, Australia, Singapore and China. About 40 members attend a typical meeting, in person or online. There is no membership fee, but there usually are charges at the in-person events to cover the cost of food and beverages.

“Being a guy of color founding a watch club is not something that’s done every day,” Mr. Flores acknowledged. But ultimately, he said, “I wanted a place where I could meet with my friends and their friends.”

At a meeting last month, the mix of attendees also seemed more inclusive than is the norm, in terms of ethnic diversity and the percentage of women in the room. (Around a fifth of the people at the meeting, which was a smaller than usual due to the approaching holidays, were female.) The atmosphere was noticeably hospitable, with Mr. Flores circulating to make introductions and encourage conversation to make sure everyone who attended was engaged. “I want it to be a welcoming and inclusive community,” Mr. Flores said, adding that he aims to be an extremely cordial leader.

“Henry has done so much to break those barriers down,” said Gary Shteyngart, an author who has been a member for about five years. “Because he’s such an effusive host, nobody feels like they’re in a world that has any chance of ever rejecting them.

“He’s just a real leader in a group that doesn’t have natural leaders — who’s going to be the leader of the watch nerds?” he said. “But he kind of stepped into that role and does it beautifully.”

Hidden underneath his sweater at last month’s session on a chilly evening, Mr. Flores wore a top that he dons at virtually every Classic Watch Club gathering: a T-shirt with the words “Cult Leader” in big letters across the chest. “Being a part of a watch community can be a little bit cultlike,” he said.

The group’s members say they appreciate the club’s inclusiveness.

“I could relate to a person like Henry who came from less of, let’s say, a privileged background,” Joyce Solano, who is of Costa Rican descent, said in a phone interview from her home in New Canaan, Conn.

“When I had gone to many of the watch events, there was a bit more of an archetype,” she added. “This group broke a bit more of those boundaries in terms of where folks came from.”

“It’s not a very diverse hobby unfortunately,” Mr. Flores said of watch collecting.

It can also seem intimidating to people without big collections or budgets. At Classic Watch Club, however, “we’re not judgmental and we don’t try and exclude anyone,” he said. “I love the hobby; the people I surround myself with love the watches as well. It’s all about the watches.”

Experts say that a broad range of members with a shared interest is a recipe for an especially successful meeting. The ideal gathering “is when everyone looks different, and everyone has different backgrounds, but they all share a passion,” said David Siegel, chief executive of Meetup, a New York City-based website and app that helps people organize get-togethers of people with shared interests. (Mr. Flores’s group is not affiliated with the company.)

Mr. Flores was born in San Francisco de Macorís, in the Dominican Republic, and moved to New York City with his family as a young child; his mother, a retired home health care worker, still lives in their original apartment.

As a teenager, a school counselor told him about Student Sponsor Partners, a nonprofit organization that helps underprivileged children in the city attend private schools; with its assistance, he graduated from a local Catholic high school. (Mr. Flores is active in fund-raising for the organization, and he said that more than a third of Classic Watch Club’s members have contributed to it.).

He earned a bachelor’s degree from Middlebury College in Vermont in 2001, and a Master of Business Administration from New York University’s Stern School of Business in 2017.

He started his career as a financial analyst — “It was a good way to build a foundation and a résumé,” he said — and now is an executive at a pharmaceutical company.

Mr. Flores said that he kept his watch collecting separate from his professional life and didn’t wear his more extravagant timepieces, like his Royal Oaks, to work. Instead, he leans toward wearing one of his Omega Speedmasters, or a piece that’s vintage and weathered instead of modern and pristine.

“People just look at it as a beat-up old watch,” he said. “I try to stay under the radar.”