Do two Omega equal one Rolex ?

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Steel C case Constellation, grey dial on a brick bracelet or perhaps a steel LeCoultre bumper with Arabic radium dial.
 
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Steel C case Constellation, grey dial on a brick bracelet or perhaps a steel LeCoultre bumper with Arabic radium dial.
Like this?
 
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Or this...fluted bezel ties it back to the DJ.

 
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Vintage diver watch with nice pumpkin tone lume. So many good ones under 1.5k. I like the super compressors from any brand.
 
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A DE VILLE Prestige chronograph would do dressy and a cal 861 or a DYNAMIC chronograph would do chronograph and a bit of military.
Edited:
 
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Explorer 36mm would be a nice contrast to what you've got now.
 
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This thread reminds me that I have lived decades past the best years of my life completely unaware that there are people for whom "what watch shall I wear in the pool" is a question they ask themselves. No criticism intended, I just never knew this was a thing.

Never a question, I know which is my pool watch. Truth is, minus showering I always have a watch on my wrist. One time I went to work without one, I was so out of sorts everyone agreed it’d be best if I just went home.
 
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If you want a quartz. 🍿

Possibly one of the only ones worth having, along with the Bulova Precisionist (styling sucks) or a Speedmaster X-33.

Tom
 
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How about a rail track constellation?

Watch sadly doesn't belong to me =(

 
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That Grand Luxe Pie Pan... the solid gold dial is stunning!
 
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While I am a rusted on chronograph fan, in this instance I would probably opt for a waterproof diver, for, beach, pool, sailing, swimming and the great outdoors in all its' glory.
My go to waterproof watch used to be a Watchco Seamaster 300.

Vintage looks with robust character. Well, it was until someone made an offer I could not refuse for that watch. Now it's a Seiko SKX007.

Love the Seiko, wish I had kept that Seamaster.
 
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I would ditch the Rolex and add a 36mm steel Seamaster Day-Date 168.023 and a Chronostop Pilot with Roulette bezel, like this .