trip-flop Share definition Flag Tripping or stumbling as a result of wearing flip-flops. Carl: "How did you get that gnarly sprained ankle?" Lenny: "Man I trip-flopped down the stairs last week". trip-flop by C-Murdah September 7, 2007 0 0 Get merch Get the trip-flop mug. Buy Now — $32.95 See more merch