I was really into watches as a kid. When I finally got some decent pay packets I treated myself to a Rolex. Since then I've bought 4 more and will wear / trade them for enjoyment.
Asking what watch to buy is such a wide question! The first question I'd ask is what you are going to use it for? Before some wag says "to tell the time", every watch does that, most mechanical watches offer a 'complication'. These range from Date, Day, 2nd timezone (GMT) or stopwatch etc.
Also you want to consider which brand to buy if you want to get your money back. Watches are not good investments, but buying the right ones can just about be inflation proof. Personally I've gone for a blend of what I like and what I think will do better than my bank interest rate over the next 10 years.