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Sperry Wool Boat Shoe

When is a boat shoe not a boat shoe? When it's made from wool. The Sperry Wool Boat Shoe ($90) takes the company's traditional boat shoe and moves it into decidedly urban territory, replacing water-friendly uppers with gray heathered wool, while retaining the rust-proof two-eyelet lacing system and rubber outsole. Pair with some Nautica gear for an over-the-top wannabe sailor look.