From my current set, I don't think I'd part with these two... they would cover most eventualities in all truth!
And if you are allowed a quartz for proper bashing about...
One watch, easy to do, more than that is just obsessive IMO (even though i do have more than 1).
For sheer ability to function without me worrying about it, id go wtih a casio g shock 5610. tough solar, multiband to keep it in time. Just buy it, use it and forget about it.
If looks come into it, SARB017. 200m water resist but still slim enough for a shirt and looks good on leather strap, bracelet and nato.
Fairly easy to get serviced and being seiko, with a bit of luck it will go 10+ years between services.
I just don’t think I could do it. Different occasions require different watches!
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Can I exclude my Garmin on the basis it’s a ‘fitness tracker’ rather than a watch?
A Rolex datejust and Casio gw5000 would cover most of my needs.
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I’m not sure if I could deal with only two watches for the rest of my life - tastes change, but for what it’s worth at present I find myself wearing only these two, and it has been that way for the last couple of months. The Monster might go in favour of something a little smaller though.
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Personally, 1 watch, simple - my apple watch, does everything I could ever ask of a watch (tells the time, perpetual calendar, 2nd time zone, accurate, water resistant, moonphase if i want it, etc.) and a lot more (fitness, notifications, heart rate, etc.) It has zero soul, history or personality but as a practical gadget it excels.
However life is never that simple.
Once the single watch barrier is broken I'd need at least:
a diver - (Breitling superocean heritage in blue with mesh bracelet) probably the most versatile diver ever (imho) good with board shorts or in the board room,
a gmt - Would have to be some sort of true GMT, Rolex is the obvious answer but I'd probably go for something Grand Seiko shaped, or maybe a ball worldtimer.
a dress watch - No idea, a Patek Calatrava is the knee jerk but price rules it out personally, maybe a cartier tank or GS snowflake,
a chronograph - Again obvious contenders are Daytona and Speedmaster but again I'd probably eschew these for something from GS or Breitling, a navitimer or chronomat, or just maybe an El Primero
a beater - easy, Smiths PRS-25 Everest.
of course once this point is reached all bets are off and backups would be required, just in case...
I manage with three watches,
Omega Seamaster, 120M, predecessor to the Aqua Terra, for everyday wear.
Rolex Submariner 14060M for more casual wear.
Omega SMP300 quartz for holidays, beater, etc.
I could quite happily manage with just two as I wear my Seamaster 120M 90% of the time.
If I had to get rid of one it would be the Submariner which I wear the least.