Sperry Top-Sider A/O in Chocolate. - size 9.5 (also in ) Sperry Top-Sider A/O in Chocolate. - size 9.5 (also in ) Leather upper with rubber sole. Leather shoe lace. SPER-MZ32. 195214. Sperry Top-Sider has been an American favorite since 1935 when Paul Sperry, inspired by his dog Prince's ability to run nimbly over ice and snow, used a pen knife to cut siping into the outsole of a rubber sneaker. This ingenuity, along with the iconic inspiration of other design details, launched an American Original.