MICHAEL WILLIAMS, who runs A Continuous Lean, a men’s style blog, ditched his Timex when he got his first cellphone in 2001.

Tyler Thoreson, the head of men’s editorial for Gilt Man, the flash sale Web site, often kept his forgettable watches stashed in a drawer.

And Eddy Chai, an owner of Odin New York, a downtown men’s boutique, gave up wearing watches regularly in his mid-20s, when he outgrew his Casio.

But after going watch-free for much of the last decade, the three men — all in their 30s and considered style influencers — are turning back time. Mr. Thoreson, 38, is shopping for a vintage gold IWC with a white dial or a Rolex GMT-Master. Mr. Chai, 38, has been wearing a vintage Rolex, loosely dangling around his wrist, “not as a timepiece, but as a piece of jewelry,” he said.