Caesar was considered a 'hipster' in his time (prior to his conquest). He supported plebian donatives and programs, which created a populist support base but engendered distrust and hatred from the Optimates (conservatives). He was also said to have a different style of dress than was the norm.
Greek culture and language were a prestige thing in classical Rome; they were practiced by the very upper crust of society. There's a reason Julius Caesar's last words were said to have been in Greek.
I don't think hipsters have achieved quite that level of glamour.