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After a certain period of time (depending on what type of waterproofing substance is being used) yes if the waterproofing is on the outside. If you have a lining on the interior of the shoe or boot (Gore-tex does this a lot) then you will very, very rarely ever have to refresh this waterproofing layer. In that instance, the outside of the shoe will become wet, but the interior will stay dry.

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Q: Do waterproof boots need additional waterproofing?
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Do timberland roll top boots need regular waterproofing?

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Maintaining a Waterproof Boot?

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Is there a company that does basement waterproofing?

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