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Any design that is dated without "looking dated."

Rolex sports models/Genta designs/Calatrava style watches (2-3hand dress watches in general)/Pilot watches/etc.
 

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It appears we are in the realm of sport watches so the thus fair unassailable leader there would be Rolex, though I am not a personal fan. Of the watches you listed the Omega SMP. The Breitling is a Breitling with all its quirks, the PO IMHO won't last as long since it is thick and large, taste will swing back, and the Carrera isn't a classic Carrera so it has less chance, a Monaco would be a better choice in the Tag line. Simple elegance (I know that is redundant) is what will always win the long term race.
 

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I love how you started out with the non-obvious choices and completely agree with you. Pretty much any yawner with sticks and a date window will never go out. I'll say the Navitimer or Daytona for a chrono. Someone else can bring up that other Omega we hear about sometimes.
 

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Rolex Submariner

rolex-submariner-116610LN_LRG.jpg


Patek Philippe Calatrava

569520d1322858429-your-dream-two-hand-time-only-manual-wind-wristwatch-5120j.jpg


Omega Speedmaster Moonwatch

35705000-30.jpg


Casio G-Shock GW-5000-1JF

gw5000c5002.jpg
 

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Omega Speedmaster Professional and Rolex Submariner (no date/cyclops).
 
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