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.

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