1. Harry Winston’s “Ruby Slippers”: $3.000.000 These shoes were designed by Harry Winston to celebrate the 50 year anniversary of the Wizard of Oz. Harry Winston’s “Ruby Slippers” are worth $3.000.000 and were decorated with over 4.600 gemstones. They are, along with Stuart Weitzman’s “Rita Hayworth” Heels, the most expensive shoes in the world.