nippleshoe Share definition Flag the new asshat..... to have a mouth so full of shit that you might actually use the word asshat. Director Kevin Smith, who popularized the phrase asshat, is a real fucking nippleshoe. nippleshoe by sanfordthefourth June 15, 2006 0 0 Get merch Get the nippleshoe mug. Buy Now — $32.95 See more merch