I am wearing an Omega Chronograph from the 60s. Paid about $600 for it about 10 years ago, but they go for about $3000 now.
Check out
www.watchyouseek.com for decent inexpensive watches. One of my favs is the re-issue of a Chinese Air Force watch for $200. Change to a leather strap and it will be derssy.
http://www.watchunique.com/index.php/featured/1963-air-force.html
Exceptional watch for the price. Nicely made column wheel chronograph movement (see Omega Broad Arrow), classic design.