As an owner and the creative director of the British shoe brand Grenson, Tim Little always wears his own designs. But frequently, he said, he notices people bypassing his feet to admire what’s on his wrist: a 39-millimeter stainless-steel TAG Heuer Monaco.

“People look at it in meetings — I can see them looking at my wrist,” Mr. Little, 61, said during a phone interview from his house in Rye, about 70 miles southeast of London, where he and his wife, Julia, also have a home. “People come up to me and ask me about it, or people say, ‘I’ve got a watch like that’ or ‘I used to have one of those’ or ‘I love the Monaco.’”

Mr. Little has owned three of the distinctive square-case timepieces, but not at the same time: The first, a gift from his wife, was stolen, and the second disappeared on a business trip. “Ever since I first wore a Monaco, I’ve never been able to do without it,” he said. “It’s something that’s really important to me.”

He said he became aware of the Monaco about 35 years ago, when the original model — introduced by the Heuer brand in 1969 and produced for less than a decade — was all that was available. (Heuer was acquired by the TAG Group in 1985.)

“I couldn’t have afforded one of the original ones,” said Mr. Little, who was working in advertising at the time. Besides, he added, “there was no real internet back then, so finding one would have been impossible.”

He settled on a rugged TAG Heuer 2000 dive watch, purchased for about 1,000 pounds at Harrods, that he tends not to wear these days.