Chaplin's hat and cane - synonymous with his trademark "Little Tramp" character in films such as "City Lights" and "Modern Times" - are expected to fetch between $40,000 and $60,000 in the November 18 auction.
It is unknown how many of Chaplin's bowlers and canes still exist, said Lucy Carr, a memorabilia specialist at Bonhams. The ones up for auction come from a private collection but have a direct link to Chaplin, Carr said.
The waddling and bumbling Little Tramp character propelled Chaplin to global fame. The character, which Hollywood legend says was created by accident on a rainy day at Keystone Studio, first appeared in 1914's "Kid Auto Races at Venice" and lastly in 1936's "Modern Times."
Chaplin's hat and cane are the highlights of an auction of popular culture artifacts including a saxophone that belonged to jazz pioneer Charlie Parker ($22,000-$26,000) and a handwritten letter from John Lennon in which The Beatle sketched himself and wife Yoko Ono nude ($18,000-$22,000).
Other items hitting the block range from an archive of Marilyn Monroe photographs ($15,000-$20,000), an early Charles Schulz "Peanuts" comic strip ($10,000-$15,000) and a wicker chair from Rick's Cafe in "Casablanca" ($5,000-$7,000).