Which watch to wear! How do you decide?

My partner asked me how I choose which watch to put on every day, and now I'm wondering how others choose. How do you decide which to wear if you own more than one watch?
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There’s another category of “feeling it”. Hard to explain, but sometimes I’ll put on a watch and I just don’t feel the connection, even if it seemed like the most logical one for the day. So I’ll cycle through and go “ah, there it is.“ 

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First A ,then B.

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I'm all about what it'm wearing.... not saying that i'm stylish (i do try) but if i'm in a suit for an important meeting then i wear something that on a strap that's discreet, off swimming or adventure in something on rubber or NATO.