Top 10 Most Expensive Shoes Ever Made Antonio Vietri Moon Star Shoes — $19.9 Million. Passion Jewellers x Jada Dubai Diamond Shoes — $17 Million. ... Debbie Wingham High Heels — $15.1 Million. ... Shoes Thrown at President Bush — $10 Million. ... Harry Winston Ruby Slippers — $3 Million. ... Stuart Weitzman Rita Hayworth Heels — $3 Million. ... More items... Jun 21, 2022