2. Hank Williams
Widely considered the greatest country music singer of all time, Hank Williams only lived to the age of 29 but left a lasting legacy of music and style. When the most prominent country singer starts donning Nudie Cohn suits, anyone who was paying attention in Nashville was going to start jocking his steez, giving rise to one of the more colorful trends in recent history. Hank put country music and its unique style on the map for good.