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This is a most ridiculous way to answer this but are they traditional boat shoes or "water shoes" boat shoes - the kind of shoe literally made to go into the water and get wet? [It's ridiculous, but for some reason, different kinds of "boaters" - from my dad the kayaker to those the ones with the engines all describe different shoes as "boat shoes."] If they are traditional boat shoes with rubber soles and leather uppers that are oiled, they are traditionally worn with no socks, but can also be worn with low-cut ankle socks, no show socks and crew socks in a poly-mix or cotton if you cannot live without your socks (depending on your activities.) Your feet actually breathe better without socks when wearing leather shoes, so I've never understood the socks + leather shoes thing. Shoes made to go in water? No socks or get gortex socks. I mean, have you ever had wet socks on your feet? * shudders *