A trove of Marilyn Monroe's belongings including handwritten letters, shoes and jewelry is expected to fetch up to $4 million when it goes under the hammer in Los Angeles in November.

More than 500 lots of her personal possessions -- the largest collection ever offered for auction -- are being sold by the estate of her acting coach, Lee Strasberg, who died in 1982.  

"Marilyn was a complex and beguiling figure in her lifetime, leaving generations of adoring fans to speculate, infer, and debate about her life," Strasberg's wife Anna said in a statement. 

"What has resulted is a prismatic kaleidoscope image built upon both fact and fantasy."

The collection includes an alligator skin men's accessory case owned by Monroe's second husband, the baseball legend Joe DiMaggio, as well as a number of Monroe's handbags, fur coats, cigarettes and a tube of used Revlon lipstick dated from 1947.

"This is one of the most important and historic auctions of Marilyn Monroe ever. This diverse collection gives us a most intimate glimpse of the screen legend," said Martin Nolan, executive director of Julien's Auctions. 

"Never before have there been so many important artifacts from the life and career of the much loved global icon Marilyn Monroe." 

Bidders will also have a chance to buy a number of revealing documents, including a taxi receipt from 1960, tax returns, recipes and a checkbook containing filled out stubs from 1962 -- the year she died.

Strasberg -- considered the father of method acting -- worked with a host of stars including James Dean, Richard Harris, Dustin Hoffman, Jack Nicholson, Al Pacino, Jane Fonda and Robert DeNiro. 

He developed a close friendship with Monroe, who bequeathed all of her personal effects and clothing to him in her will.
The collection will tour Europe, Asia, South America and the United States before being sold off on November 19 and 20.

Monroe, one of the world's most bankable stars before her death aged just 36 in Los Angeles, remains at the top of the list for collectors of celebrity memorabilia.

Julien's Auctions announced in April it would be offering a selection of the star's costumes, personal gowns and jewelry valued at $3 million, including the cocktail dress she wore in "Some Like It Hot."

Five years ago, the billowing frock she wore on a subway grate in "The Seven Year Itch" -- the scene that turned her into a screen icon -- sold for a record $5.5 million.