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Which watch has been in your regular rotation for the longest time, and how does it stand up to later arrivals?
For me it is the Breitling Superocean 42 which was my first 4-figure purchase, and is coming up for 5 years now. Many others have come in (and some have gone back out again) but the SOH is still a favourite.
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Hamilton Kakhi field quartz, my father bought it to me when I graduated 2003, that is a bunch of years actually. I used quite a lot in my firsts years at work. I still use it a couple times a month, not just for the melancholia, it is a good and beautiful watch.
 

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The Seiko Tuna. I'll never sell it, but if I'm being honest it rarely gets wrist time. It recently got new shoes and I think it looks the best it has ever looked, but I no longer have much of a yearning to wear it.
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had it since 2014 but officially retired from rotation. I thought about selling it due to the boost in value but I probably won’t.

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The first generation Smith & Bradley Ambush. I bought it because I wanted a watch that could give me multiple time zones easily, and ended up with an awesome piece of gear with great WR (100M) that I could swim with and time laps, have a third time zone on call, and a few other handy features. It has been on my wrist every time I fly military, and I haven't found anything that's a direct replacement.

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Casio GW6900. Only because it’s too cheap to sell it and it’s bullet proof. Probably had it 10 years or so.

Once I thought it was dead and was excited about replacing it, but then I let it charge in the sun. Been 2 years since then.
 

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My bulova marine star auto with skeletonized version the often insulted miyota 8215, a birthday gift from my mother in 2010.
I opened it recently to wipe off the haze on the inside of the glass and it still is a favorite in my rotation, either on a nato or the stock bracelet.
I've used sand paper to refinish the bracelets brushing about 3 times.
Still very accurate to this day.

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Mines a G-Shock G100. It's at least 15 years old. So old the plastic has began to rot. Original battery. This watch has seen some things. Maybe one day I'll source a case cover. The current ones are called Baby G's. Until then. It resides with some other keepsakes.
 

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My longest owned regularly worn piece - 2 liner Pelagos. 5 years and counting which is a lifetime for a serial flipper such as myself. It’s traveled w me everywhere and keeps on keeping on.

I’ve had many a more expensive piece but I always end up wearing the Pelagos.

 

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My citizen eco drive. 23 years ago my mother gave it to me as a birthday present. Still going
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somewhere around I think I still have my first watch, a Swiss army watch that was being given away in the Marlboro miles campaign. I made all of my smoking relatives save all their cigarettes packs so I could get that watch. I was 12 or 13 at the time and was so excited by how much everybody smoked. The watch was not the only thing in the catalog I managed to get either. Shows the power of marketing
 

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Which watch has been in your regular rotation for the longest time, and how does it stand up to later arrivals?
For me it is the Breitling Superocean 42 which was my first 4-figure purchase, and is coming up for 5 years now. Many others have come in (and some have gone back out again) but the SOH is still a favourite.
View attachment 16117072
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When I receive a new incoming, it’s the typical 2 month honeymoon phase, however I always end up coming back to this. Which also happens to be my longest in service
 
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