cup cankles Share definition Flag its where the person is so fat, that they have a layer of fat drooping over their cankles forming the shape of a cup cake. look at the cup cankles on that fat lady!hey dude, cover up your cup cankles. cup cankles by The Iraqi Beef March 23, 2011 0 0 Get merch Get the cup cankles mug. Buy Now — $32.95 See more merch