About 30 years ago I inherited my Grandfather's gold 1966 Seamaster Cal 562. That was the start of my Omega collection. In fact it was Omega Constellations that really got the Omegamadness going. I have 5 Connies 2782, 2852, 168.005, 168.018 and Manhattan. There are a variety of Seamasters ranging from Cal 269, Titane ref 1420 to SMP 2531.80. Most of my collection is vintage and ironically, my Speedmaster Pro, which is such a classic Omega, is modern - bought in 2012.
I have a soft spot for Tissot Seastars and also have several Longines Automatics from the 50s and 60s
I adore chronographs and together with my Speedy, I have IWC Pilot Chrono 3717, GST 3707, 1960s Bovet and a series of Nivadas including Chronoking Aviator Sea Diver, Grenchen Chronomaster, TDBK from the 1970s and a Skymaster.
I am keeping over 30 watches in rotation, worn 3 days at a time. I have the addiction pretty bad! Oldest watch is Rolex Speedking from 1948.