The Starter Rolex: Where a Gentleman Begins

Four watches, one decision, and the quiet case for buying the right one first.

A steel dive watch on the wrist, whiskey at hand

There's a moment, usually somewhere in a man's thirties or forties, when he notices that the watch on his wrist no longer matches the man wearing it. It isn't a crisis. It's simply time.

For a great many of us, the answer is a Rolex. Not because it's the most complicated watch in the world, and not because it's the rarest. It's the one that has done the same job, quietly and superbly, for most of a century. A good Rolex looks as right with a dinner jacket as with a fishing jumper, and it'll still be running when your grandson inherits it.

The difficulty isn't wanting one. It's choosing well. There are four sensible places to begin, a handful of sizing questions worth taking seriously, and a buying market that rewards the patient and punishes the hurried. Let's take them in order.

R. Ashby
R. Ashby

R. Ashby writes for Madison Hour. He wears a gold watch, smokes a Davidoff when the evening allows, and answers his letters by hand. He prefers not to say much more than that.