I don't really understand what that means in the current sense. When I was young being "hip" meant you knew and understood and appreciated things that most people did not. Such as jazz, classical music, Zen Buddhism and other Eastern thinking, some foreign films and novels, etc. "Hippies" in the original sense were people who tried to cultivate hipness - to act hip whether they were or not. Then later, from the later 1960sm "hippies" came to connote those of us who dropped out of conventional society and lived alternative lifestyles.
Buddy Holly, as far as I can understand was just a good old boy trying to make it. Country and rock and pop were the extent of what he cultivated. More famous in death than in life.