Rolex Yachtmaster 37

The Yacht-Master takes the whole sports-watch idea and puts it in deck shoes. At a glance it looks like a diver, but everything's dialed toward leisure rather than duty: a raised bezel in precious metal or ceramic, softer color pairings, and the general air of a watch headed somewhere with a better view. You'll find it in steel, two-tone, gold, and even a rubber-strapped version you could actually take on the water. There's also the Yacht-Master II, a big, unmistakable regatta chronograph with a programmable countdown for timing race starts. Of all the Rolex sports watches, this is the one least interested in pretending it's a tool, and the most comfortable admitting it's here to have a good time.