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Will I regret wearing Converse All-Stars for a work basketball league?

If you mean the old canvas kind with zero ankle/arch support then yes its a very bad idea unless pain is somthing you enjoy ... on the other hand if you mean the newer ones they are a little on the heavy side but not all that bad.
 
At least get some quality inserts. I can't even wear those things without inserts, period. I have a couple pairs, but I try to avoid any physical activity in them. I carry some Nike Airs in my trunk in case I need to bust out the moves at work.
 
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