How important is it to match your watch with your outfit?

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It shouldn't clash or have a formality gap. I'm prissy with coordination and complementing on other haberdashery accessories, but usually not with watches. Although I definitely will sometimes swap in a single pass fabric strap that coordinates well.

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rules are match the strap with belt or the shoes 😂. but that is just me

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I choose my watch without regard to my clothing. 

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Dave you are a barbarian.  I agree with Oscar's take, never clash but if you can't match it, contrast it.  https://drive.google.com/file/d/0B7FvB7tbnjTaNWI5NmUyZDYtOWJlMy00M2NmLTkxYjctNDBlMGJiNDJkNTc2/view?hl=es&authkey=CJ7hsPcM&resourcekey=0-cUhGJRrAnrG4zTxp_ESV5w