Reynolds, 79, who starred opposite Gene Kelly in Singin' in the Rain, said she was "a fan who was lucky enough to be among stars, so I collected them".
Dame Elizabeth's Cleopatra headdress will be included in Saturday's sale.
Auction house Profiles in History said the 600 lots at the Beverly Hills auction could fetch up to $10m (?6.2m).
Dresses include those worn by Marilyn Monroe in Gentlemen Prefer Blondes (l), and River of No Return (r) Reynolds began her collection at a 1970 MGM auction of props and costumes and also bought items at Fox and Paramount studio sales.
Prize lots include Hepburn's black-and-white gown from the Ascot racing scene in My Fair Lady, designed by Cecil Beaton and Monroe's dress that was caught by a gust from the subway in the Seven Year Itch.
Items associated with Dame Elizabeth - who singer Eddie Fisher divorced Reynolds for - feature prominently.
The two became friends in later life, and when a costume worn in Cleopatra by Dame Elizabeth's ex-husband Richard Burton came onto the market, Reynolds persuaded her to fund the purchase.
Other outfits offered in the auction, which will also be conducted online, include those worn by Marlon Brando in Mutiny on the Bounty, Yul Brynner in The King and I, and Greta Garbo in Anna Karenina.
The sale also includes a guitar played by Julie Andrews in The Sound of Music.
Reynolds, whose daughter is actress Carrie Fisher, previously housed her collection in her combined casino, hotel and museum in Las Vegas which she sold in 1999.
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