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This story is from an installment of In the Loupe, our weekly insider newsletter about the best of the watch world. Sign up here. Anyone who’s ever bought or contemplated buying a secondhand Rolex ...

At first glance, any man walking along Main Street in Nantucket might be indistinguishable from a local, granted he has procured the right accoutrements—a colorful polo from Ralph Lauren, a pair of ...