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That's an old debate.
Being a vintage collector I find the Rolex production of the 1940-60s rather limited (and certainly overrated): oyster, oyster and oyster (with the odd chrono, explorer or milgauss).
Vintage Omega is great fun. Hundreds of case and dial variations -- military, sports dress and technical watches -- as well as beautiful movements make it a really fun brand to collect. A vintage connie or a midsize seamaster, a 30TRg chronometer, a Ranchero or one of the first moonwatches really stand on their own feet in terms of styling and workmanship. OK, Omega's marketing isn't as good as Rolex (Sorry, Cindy) but honestly, owning both brands, when I want to stick to good taste, I'll always wear my beautifully aged 1939 30T2 steel Omega or one of my gold and subsec dial (6-killer) 1940's cal 265 rather than my black dialed oyster, whose only cultural advantage is its water resistance. But then again, I'm not usually dumped in a pool by surprise (not any more).
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