I pick the one I feel like wearing.
I do match shoes/belt/strap, but I usually change the clothes to match the watch instead of the other way around.
Sometimes I feel "guilty" for ignoring a piece for a while, especially if it is a higher value piece (okay higher value for me, not for a lot here) but then I realize....it's just a watch. Opps! Wrong place to say that I guess.
Cheers, Al