Stuart Weitzman Diamond Dream Stiletto, $500,000 (2007)

During the 2000s, American designer Stuart Weitzman famously created a series of “million-dollar” heels for the Academy Awards red carpet. While these Diamond Dream sandals, which were worn by “Dreamgirls” actress Anika Noni Rose at the 2007 Oscars, fell short of the title with a value of $500,000, they still earn a place on the list of the most expensive shoes in the world. The silver stiletto sandals were adorned with 1,420 individual brilliant-cut Kwiat diamonds, weighing over 30 carats, with the diamonds set in platinum circles.