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I'm a fan of XtraTuff. I've seen in a lot of reviews that people will double up their socks and wear them around for a while to stretch them and break them in. Definitely hard to mitigate that soreness in the toes, especially on a long day out on the water.
Now, if you're talking about going out on a kayak, I've been working at this one for a while. I'd been wearing neoprene booties for the longest, but they just don't drain and dry from the initial wade out into the surf or provide the support I want.
I eventually settled on Merrill water shoe with a .5mil neoprene sock. Super comfortable, warm, and not as soggy as a neoprene boot.
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