Marilyn Monroe's star power is never more evident than when her memorabilia items cross the auction block, and the prices her dresses have fetched illustrate the story. Of the 25 most valuable women's dresses ever to sell at auction, Marilyn owned 13 of them.

Now the infamous see-through dress in which Marilyn famously sang "Happy Birthday" to United States President John F. Kennedy is set to break records all over again when it goes to auction a second time on 17 November 2016.

The dress is already the fifth most expensive dress in history from when it last went to auction on 27 November 1999, offered by the widow of Monroe's acting coach, Lee Strasberg.

The US$1,267,500 fetched at that 1999 Christies auction made the dress the most expensive piece of clothing ever sold at that time, so although the official estimate for the dress at the November Julien's auction has been set at between US$2,000,000 and $3,000,000, Marilyn's subsequent world record of US$5.5 million for the subway grate dress from The Seven Year Itch is under threat.

The event in which Marilyn wore this dress took place at a joint Democratic Party fundraiser and 45th birthday celebration for JFK at Madison Square Garden in New York on 19 May 1962, and it certainly became one of the most iconic moments in either her or JFK's life, when the scandalous sub-text completely overwhelmed the occasion.

Marilyn's performance that night was carefully managed for maximum impact. Her biographer Lois Banner, in her book Marilyn: The Passion and the Paradox (New York: Bloomsbury, 2012), asserts that Monroe told the event planners that she would dress discreetly.

When viewed under normal lighting conditions, the dress appeared considerably more modest than it did when the spotlights hit it. Marilyn rehearsed in elegant but casual clothes, changing into the dress just prior to the performance and wearing a white fur coat over the top of the dress until she was on stage, which prevented anybody getting a clear look at what she was really wearing – a sheer body-hugging dress without any lining, and heels.

The video of the performance above does not quite capture the full visuals seen live by the audience as it's 70 year old broadcast quality black and white, but Marilyn's dress had been color-matched to her skin tone, and the thin bejeweled (2,500 rhinestones) gown was so tight and sheer that she had to be sewn into it "au natural."

Under the Madison Square Garden spotlights, "the Jean Louis creation magically transformed into a sparkling second skin" as it was described by the auction catalogue, which is a nice way of saying she appeared naked.

Take a look at the intimate and sexual tone of the performance and you'll perhaps grasp how inappropriate this was considering that Monroe was having, or had previously been involved in an extra-marital affair with the 42-year-old President.

The gasp from the audience when she removes the fur coat is quite pronounced (1:20 on the video).

The catalogue also states: "The dress and the song were too much for the political dynasty, and according to Banner, that evening ended whatever relationship Monroe and John F. Kennedy shared and severed her from the rest of the Kennedy family."

Marilyn's over-the-top sultry performance set tongues wagging across the globe, including the halls of power. Just three months later, Monroe died of a barbiturate overdose, fueling conspiracy theories that still have tongues wagging 54 years later.

The owner of the dress, investor Martin Zweig, passed away in February, 2013 and after some deliberation over the appropriate auction house to handle the sale, the dress worn by the most iconic of sex symbols to deliver the most infamous rendition of "Happy Birthday" in history is set for auction once more.

Julien's Auctions has produced a video about the dress.

The top 10 most expensive dresses in history

In the 17 years since this dress was last auctioned, just four dresses have sold for more:

$5,520,000 | Marilyn Monroe's subway dress from The Seven Year Itch

This rayon crepe halter dress with pleated skirt by Travilla is currently the most expensive item of clothing ever sold!

It was worn in the 1955 movie The Seven Year Itch by Marilyn Monroe, who played the female lead role while Tom Ewell played the male lead. Tom now rates only a footnote in cinematic history, while Marilyn's subway grate scene became one of the most recognizable images in modern society.

One of the greatest coups in PR history was the decision to stage the publicity shoot for the media with Marilyn standing over the grate. Every photographer got their own version of the same image and it unleashed an epidemic of iconography which propagated via newspapers, magazines and news services and burned into the global psyche, at least judged by the price. The dress went to auction with Profiles in History in 2011 as part of the Debbie Reynolds Collection.

Looking at a list of the top 200 dresses ever sold leaves little doubt that the value of a dress at auction is directly related to important moments in film history. Apart from a few dresses worn by royalty (usually Princess Diana) and movie stars (usually Elizabeth Taylor) to important occasions, they are all dresses that have been worn in films.

The only item of clothing at auction from any genre other than entertainment that gets near these prices is Napoleon's signature hat ($2.4 million), which is less than half the price of this dress.

In the male clothing area, the most significant sale behind Napoleon's hat is the red leather jacket Michael Jackson wore in his epic music video "Thriller", which went on to become the top grossing music single of all time, and the album went on to become the highest selling album of all time too. Jackson, like Monroe was a master of iconography, and following the success of the extended video for the single, he continued to use jackets of the same design when performing the song "Thriller" for the duration of his career. It sold for $1,810,000 in 2012 at Juliens.

$4,400,000 | Audrey Hepburn's Ascot Races dress from My Fair Lady

The magnificent dress worn by Eliza Doolittle (Hepburn) in her "coming out" moment at the Ascot races in the film adaptation of George Bernard Shaw's 1913 play Pygmalion. Pygmalion became a smash hit musical stage play in 1956 as My Fair Lady and subsequently enjoyed even more success as a 1964 movie in which this dress appeared. Profiles in History auctioned the dress in 2011.

$1,565,000 | Judy Garland's "Dorothy" dress from The Wizard of Oz

There have been several Dorothy Gale dresses from the 1939 movie sold in recent years, some of them that were "test" dresses and didn't even appear in the movie, but they all sold for astronomical figures, with the most valuable being sold for $1,565,000 by Bonhams in 2015. We have removed the other versions from the list, but different versions have also sold for $910,000, $666,000, $480,000 and $266,638 plus Dorothy's ruby red slippers and the Lion's costume have both sold for more than $3 million, so the appeal of this dress appears to be based partially on the landmark movie, and ... whatever it is about the dress, it clearly resonates with the public on a very powerful level.

$1,476,000 | Marilyn Monroe's showgirl gown from Gentlemen Prefer Blondes

The red-sequined showgirl gown Marilyn Monroe wore alongside Jane Russell in Gentlemen Prefer Blondes, fetched $1,476,000 at a Profiles in History auction in June, 2011.

The following dresses fill out the top 10 most expensive dresses ever sold at auction:

$923,187 | Audrey Hepburn's "Little Black Dress" from Breakfast At Tiffany's

There's some legitimacy about the "little black dress"Audrey Hepburn wore in Breakfast at Tiffany's appearing on this list other than as a movie prop, as it is a fashion landmark. Designed by Hubert de Givenchy, the dress has become iconic in the fashion world and although US$923,187 is a lot of money, the influence of THAT dress has been immense. It sold for £467,200 at a Christie's London auction in 2006 (we calculate all prices in American dollars on the exchange rates on the day of the sale, including all commissions).

$660,000 | Julie Andrews Do-Re-Me dress from The Sound of Music

Do-Re-Me is a song that has been sung countless times by billions of children and it's arguably the most watched instructional clip of all time. It was written for the 1959 Rodgers and Hammerstein musical The Sound of Music and when the movie of the same name came out in 1964, the song was a radio hit and yet another generation imprinted the notes of the major musical scale while they sang along, just as the Von Trapp children did in the movie. This is the dress Julie andrews wore in the filming of this timeless classic. It sold for $660,000 at a Profiles in History auction in 2013. The rest of the wardrobe for the film sold for $1.56 million.

$627,300 | Marilyn Monroe's gold Travilla saloon-girl gown from River of No Return

One of three very distinctive dresses from this film on this list, the gold Travilla gown sold for $627,300 at a Profiles in History auction in 2011.

$553,500 | Grace Kelly's dress from To Catch a Thief

Worn by the movie star who really did become a princess, Grace Kelly's dresses appear numerous times on the list of the top 100 most expensive dresses sold at auction, most notably for the "Princess Alexandra" ivory silk chiffon evening gown by Helen Rose she wore in The Swan, which fetched $135,300. As a fashion icon, he accessories sell for astronomical prices too – such as the Givenchy hat she wore in Funny Face ($87,500).

In the 1955 movie, To Catch a Thief, Grace Kelly starred opposite Cary Grant and the dress she wore often in the film sold at a Profiles in History auction in 2011.

$526,000 | Marilyn Monroe's green Travilla saloon-girl gown from River of No Return

One of three very distinctive dresses from this film on this list, the green Travilla gown sold for $526,000 at a Profiles in History auction in 2011.

Plus two more contenders

Marilyn Monroe's Red sequined dress from River Of No Return

This dress went to auction in 2014 with an estimate of $400,000 to $600,000 and failed to meet reserve. It went to auction again last year with an estimate of $300,000 to $500,000 and again failed to meet reserve. It's the signature dress from the film which contributes two other dresses to this list and ... we think it will be on the list sooner or later.

Marilyn Monroe's Cocktail dress from Some like it Hot

This dress is to be auctioned at the same time as the "Happy Birthday" dress and is expected to fetch $400,000 to $600,000. It's the signature dress for the movie Some Like It Hot (and worn in the poster) and clearly another contender for the top 10 list.

The final word

"If something looks too good to be true, it usually is (not true)" goes the adage, and you'll note that nearly all the prices on this list are for items sold in the last five years. The auction marketplace for entertainment and sports memorabilia looks like the perfect marketplace as it has grown relentlessly for the last decade.

Will these objects which are iconic to one generation but perhaps not the next, drop in value at some point when the demand dies off? Will memorabilia forever exploit the laws of supply and demand, or will demand diminish with generational change.

Depending on the genre, it's very unlikely that demand will relent because these objects are sought by museums and other institutions that safeguard our heritage. Items of cultural significance should continue to grow in value over longer time frames.

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