What would you pay to be in Hugh Hefner’s shoes?

For the third time, Playboy founder Hugh Hefner, 86, separated from his trademark red robe long enough to marry. He wed Crystal Harris, 26, on New Year’s Eve in a tuxedo.

And it’s not just his robe. There are a host of material possessions that come to mind every time the octogenarian is mentioned: a captain’s hat, smoking jacket, loveseat, racy artwork, and bunny costumes.

Then there’s the Playboy Mansion, the Neverland of debauchery and decadence.

There’s no doubt Hefner’s pre-nup agreement has got it covered, but it’s hard not to wonder which of his possessions will instantly become coveted trophies for memorabilia hunters if he were to give up the ghost.

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Those who make a living out of trading memorabilia are certainly not indifferent to the golden investment opportunity the proposition represents.

If Hefner were to die, “There are many things associated with him that would [quickly appreciate] in value,” says Darren Julien, president and CEO of Julien’s Auctions in Beverly Hills, California, the city Hefner calls home.

“The most iconic things would be anything relating to the first issue of his publication, because Marilyn Monroe was on the cover and the feature story.”

That first issue was the beginning of what was to become a multi-billion-dollar adult entertainment empire.

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It’s only expected that Hefner has a large archive of magazine-related works he’s collected and preserved along the way.

While it’s hard to tell what’s in his archives, Julien says there are items Hefner possesses that are not difficult to imagine due to their iconic status.

Here is a list of some of those items and what Julien reckons they would be worth when the paragon of hedonism has had his last puff.

• The iconic robe: $2,000 – $4,000
• Smoking pipe: $3,000 – $5,000
• Original Playboy card from Chicago: $4,000 – $6,000
• First bunny costumes: $5,000 – $8,000

“I know they have other artifacts in their archives that would be worth a lot more, like original pin up art. Some of them could sell for anything between $20,000 and $60,000,” says Julien. “However, they’re not as interesting as his personal artifacts.”

The articles that have sold for the most are those from the Chicago Playboy Club where Hef first got started, he adds.

Investors who like the idea of adding atypical assets to their portfolios must note that although these price tags come from a memorabilia expert, they’re only estimates.

The actual price range may vary depending on such factors as demand, condition of objects and the length of time before they are up for grabs.

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