Fedora Worn By Michael Jackson

Michael Jackson wore this fedora hat in the 1984 music video for "Billie Jean." A year later, it was sold for a whopping $350,000. It has been described as a pop culture icon, so much so that other celebrities have tried to buy it, including Justin Timberlake and Kanye West. However, both of their bids were unsuccessful due to bidding wars between themselves, which drove up prices even more until they were finally outbid by a wealthy Saudi Arabian investor.

This fedora hat is a black fur felt fedora with a gold metal buckle on his Victory tour in 1984. The interior is lined with white silk and bears the Maddest Hatter's symbol, a double Griffon flanking a crest with the banner "A Crown Upon Your Head." "Manufactured in USA custom made 7 3-8," reads the inner label. "By Maddest Hatter"; "Made Expressly for Michael Jackson"; "100% Genuine Fur" are stamped on the internal black leather hatband.

Although the titfer has no distinguishing features, it became invaluable when Michael Jackson put it around his head on stage at Wembley Stadium during one of his performances.

Price: $56,250