I've favored drain holes in anything which regularly gets filled with water--this includes pockets of all outerwear, along with footwear designed to be worn in rain or stream-crossings. Boating gear is generally designed this way, and it's been a mystery to me why motorcycling outerwear is not.
Drilling holes for ventilation had not occurred to me, but I guess I'm going to have to try it. I wouldn't do this in boots which keep my feet dry under water, but if they're going to collect water anyway I want to provide a way for it to get back out again.
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