Sperry or Sperry Top Sider is the original American brand of boat shoe designed in 1935 by Paul A. Sperry, older brother of writer and illustrator Armstrong Sperry, whose books often featured a sailing theme. Sperrys, or Top-Siders, were the first boat shoes introduced into the boating and footwear markets.Sperry or Sperry Top Sider is the original American brand of boat shoe designed in 1935 by Paul A. Sperry, older brother of writer and illustrator Armstrong Sperry, whose books often featured a sailing theme. Sperrys, or Top-Siders, were the first boat shoes introduced into the boating and footwear markets.