Men's jewelry is a touchy subject, some men can make it work, most won't even try. But if you feel inclined, I highly recommend the attempts. There are many ways to start, but one of the ones that can be easily attempted and accomplished is with David Yurman bracelets. Some of his stuff is audacious and overly feminine, but other pieces have just the right amount of masculine charm and classic looks to be effective for your first foray into men's jewelry.
Make sure you pick a piece that works with your personal style and then wear it, all the time. Get used to it and make it part of you, just like a good watch or shoes. Soon you won't want to leave home without it.