6. Charlie Chaplin Bowler Hat
Bowler hats are known to be an affordable piece of headwear but what makes this one cost $62,500 is because it was owned by the legendary Charlie Chaplin. He is known to be one of the key figures of the film industry and revolutionized a lot of the film productions we see today. The hat was famous during his time and he gave the bowler hat to a wax sculptor during the 1930s. It was only recently sold at an auction during 2012.