I can't even wrap my head around doing that every day. Then again, I rarely wear a watch.
I only make the effort with brown shoes and belt and my German pilot watch on a brown strap. Mostly I wear a stainless steel band. I will wear a black leather band with black shoes and belt. I love watches and feel naked without one.
Not far from the truth! Good friend of mine was jogging years ago and came across a watch with a broken band that had obviously fallen of the wrist of another runner. Turned out to be a Rolex GMT Master. I can only imagine the pain the original owner felt!
Actually I'm a retired Army guy. No watch means you're potentially late. Late is painfully unacceptable.
While on the subject of watch bands matching belts (and bizarre comments) one of the most bizarre comments I have ever received on Styleforum (and the commenter later deleted) was after posting this picture showing how my friend's tan alligator watch strap matched my tan alligator belt.
This would have been a better picture if my friend had followed my suggestion to turn her wrist so that more of her watch strap showed, but she wanted her watch to show. (Yes, she's wearing a bracelet that not's the same metal as her watch.) Part of my watch (the chain of my pocket watch that's in my watch pocket) also shows in this picture.
(Yes, she has many watches.)
Very similar terms in some cases. I always proceed mentally from CBD and move outward. Would not think of wearing a smart business suit with mismatched belt and shoes. I consider that matching and the watchband to be complimentary.