If we're being honest, no man needs a watch these days. With the ubiquity of cell phones, accurate timekeeping is now just an awkward fumble in your pocket away. But, of course, telling the time is merely one function of a watch. A proper timepiece, like a good suit, can make a man feel instinctively more confident because it instantly communicates an image he's trying to project. After all, you can tell a lot about a man from the watch on his wrist. Perhaps that's why some men strap on various timepieces—to switch up what they want to say about themselves. But you don't need half a dozen different watches. Invest in a quality timepiece with provenance and substance and it will go with you anywhere. We asked our friends at Crown & Caliber, the number one online marketplace for luxury pre-owned watches, this question: If you could only own one watch, what's the best option for a budding collector, or someone looking to wear one watch—and one watch only? Here are their top five.