I don't think about it much. I wear what I feel like and try to keep it on for a week or more. Most of the time cycle through the Railmaster LE, the WatchCo Seamaster 300, and Seamasterr Professional 2254.50. My 1917 Omega "trench" came out so nicely I'll wear that one fairly often as well.
Then I have a bunch that get worn rarely, like my pink gold Lemania, and my dad's Croton Aquamatic watch.
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