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Oh, I bought these in a 7 1/2, a half-size bigger than I normally wear because I always wear thick socks with boots. If you wear normal socks, your regular size . Blue Yeti Vs At2020, Do You Wear Socks with Sperrys? - Groenerekenkamer -. There are also some rules that you should know about wearing socks with sperrys. Always wear white crew length socks with boat shoes and never wear ankle high . Catergator Vs Yeti, Sperry Boots Review. 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