waterproof socks won't breathe and the sweat will gather, no way I'd do that. I'd rather just use a quality wool sock and deal with the damp than trying to waterproof it. the negatives of waterproof vs not are to high for my taste. feet need to breathe just like hands/torso/etc do. flip side to this is if you want hiking shoes get hiking shoes instead of trying to use a converted cycling shoe. the needs of both are far different and worth the investment in having both. just my .02