ruffle jimmies Share definition Flag To ruffle a person's jimmies is to taunt them by comparing them to someone who's more successful than them. Ruffle jimmiesPhil Jackson ruffled Kobe Bryant's jimmies by comparing him to Lebron James. ruffle jimmies by Asidd January 1, 2011 0 0 Get merch Get the ruffle jimmies mug. Buy Now — $32.95 See more merch