2. Paul "Bear" Bryant's Houndstooth Hat

Debuted: 1954
Famed Appearance: On the Alabama Crimson Tide sidelines, 1958-1982

In his tenure at Alabama, Bear Bryant won six national titles and thirteen SEC championships. Almost as iconic as the number-clad helmets worn by the Crimson Tide players was another signature piece of headwear sported by Bryant. His stylish houndstooth hat was certainly every bit as famous as logos of that era like Ford and Lucky Strike. Bryant earned his nickname for fighting a bear. Who would have thought that decades later the fedora would be championed by guys who look like one?