Ray Price was one of the original supporters of Nudie Cohn, and he definitely rocked some of the famous tailor's most awesome creations. He is considered one of the pioneers of 1950s honky-tonk music, and when a genre you help make popular is synonymous with bars that cater to guys who are looking to get wasted, you better dress like a party animal. Ray Price did not disappoint, and he continues to wear flamboyant clothing as he continues to ball out in his late 80s.
5. Ray Price