cadillac hippy Share definition Flag Someone who claims to hippy, but drives an expensive car; such as a cadillac. I suppose you could consider it an oxymoron. There goes that cadillac hippy again. cadillac hippy by XLR8TIN October 9, 2008 0 0 Get merch Get the cadillac hippy mug. Buy Now — $32.95 See more merch