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Neither. Clean them when they need to be cleaned but don't slave over them.
I get mine dirty, throw them in the wash and let them air dry to look as good as new. After a few washings they take on a slightly off-white look that has a certain vintage look to it. That is when I feel they are broken in.
P.S. The Cheng's plimsolls at Urban Outfitters are a nice pickup at 2 for $30. They don't last as long as Vans, etc. and are less comfy but the price is right.