The hat and cane, trademark of Chaplin's Little Tramp character, are in "remarkable condition" and are estimated to go for between $40,000 and $60,000 at the sale by auction house Bonhams on Sunday.
Legend has it that Chaplin came up with the tramp persona and wardrobe spontaneously one rainy afternoon in February 1914, seizing various wardrobe items in a communal male dressing room at a Hollywood studio.
These included baggy trousers from Fatty Arbuckle, size 14 shoes which he had to wear on the wrong feet to keep them from falling off, the hat belonging to Arbuckle's father-in-law, and a mustache intended for another actor.
The 32-inch (81-centimeter) bamboo cane is inscribed "CCLT 36" in black ink, a reference to the Little Tramp, Chaplin's signature character.
Other items on sale include a handwritten letter by Lennon with a nude drawing of himself and Yoko, sent to an avant-garde magazine publisher in connection with the controversial 1968 "Two Virgins" album cover.
The letter is estimated to go for between $18,000 and $22,000, while several other Beatles-related items are also up for sale, including a set of autographs of the four band members before a 1964 Hollywood Bowl show ($4,500 to $6,500).
A saxophone which once belonged to jazz legend Charlie Parker has a reserve price of $22,000 to $26,000.
Also on sale are various items related to Marilyn Monroe and three signed, abstract original oil paintings by crooner Frank Sinatra.