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Add a Chrono and a GMT.
 

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You have a lot of great suggestions but I think the thing to guide your choice is, why do think your collection’s lacking? If it’s just because you’re going number I’d say don’t bother. If you can get more specific about why, even if you don’t quite know what, it would narrow your choices considerably.
 

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I’m reading the absence of Rolex as intentional. Rather than a Daytona, I’d go for something with vintage style yet a bit offbeat: the Zenith El Primero A384 Revival.
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After that, I think the Breguet more than covers the “old world class” beat, so I think what the collection would need at that point is something very modern, but still elegant. Something like a De Bethune or an MB&F would fit right in, but I think what would be really cool here is a Ressence:
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Ymmv!
 
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