Hobo Toes Share definition Flag State of toes in between pedicures where the polish has chipped, faded, is missing, and/or calluses are growing out of your sandals. "I wanted to wear my stilettos today but my Hobo Toes were lookin nasty." Hobo Toes by White Cheddah February 9, 2010 0 0 Get merch Get the Hobo Toes mug. Buy Now — $32.95 See more merch