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.