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I'm lefthanded but generally wear the watch left. IMO it stems from tradition when watches needed to be winded, ever tried to wind a watch on your right arm? You've seen it like this as a kid so you just copy...
Occasionally I do wear it right and there is nothing wrong with that, although I know people that have issues in reading the time "at a glance" when the watch is on their right arm, possibly something to do with peripheral vision? Any doctor in the room?

When I was sailing I wore the watch underarms left, that way I could read the time without changing my hand position when taking a starfix with a sextant. You hold a sextant in your left hand and do the adjustments with your right, your watch is then facing you and can be read instantly. I guess the same reasoning goes for drivers who wear their watch underarms.
I stopped doing so when doing Starfixes were replaced by computer keyboard work as a main daily activity.

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