Should I waterproof my moccasins/boots?

I would suggest that you apply a good water repellent spray on suede or a leather cream on moosehide and deerskin to keep your footwear in "like new condition". If your moccasins get wet, let them "air-dry" naturally. Do not use heat sources such as stoves, campfires, hairdryers, etc. These procedures leave your moccasins dry and crisp, and unable to be restitched or resoled.

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If you don't want anyone to know, don't do it.-- Chinese Proverb