Winnie-the-pooing Share definition Flag When someone wears a shirt but no pants, like Winnie the Poo. "Dude, don't sit there, Ron's been winnie-the-pooing all over this living room" Winnie-the-pooing by Vagina, Alotta August 5, 2012 0 0 Get merch Get the Winnie-the-pooing mug. Buy Now — $32.95 See more merch