March 2016 marks a month Playboy enthusiasts might have never seen coming. That's when Playboy will stop publishing images of nude women — an iconic aesthetic that the magazine was famous for.
So, what happens when a company rebrands itself in a way that strays from its fundamentals?
According to Jack Trout, president of marketing firm Trout & Partners, "usually nothing very good."
"This is what I would call a very difficult marketing problem … a Rumpelstiltskin problem," he said. "What you're asking (Playboy) to do is to spin straw into gold."
On the other hand, Robert Passikoff, president of brand consultancy BrandKeys, told CNBC what Playboy has on its hands isn't necessarily "straw."
"It's gold that people haven't been buying, and now they've got to reposition themselves to a different audience," he said.
Passikoff said Playboy's issue is defining what the brand stands for as it revamps its editorial content. While many companies have the financial wherewithal and manpower to make big changes without a heavy risk, the issue ultimately comes down to brand believability, he added.
"The question is not 'Can we do it?' " Passikoff said. "The question is 'Can you do it in a way that's going to engage consumers?' "
Consumer engagement is a problem that Playboy has seemingly struggled with; The New York Times reported Monday that Playboy's circulation has dropped from 5.6 million in 1975 to about 800,000 now.
The ubiquity of nude images available on the Internet has significantly reduced the number of readers who pick up a hard copy of Playboy off a newsstand, Passikoff said.
"If you've got a smartphone and an Internet connection, the commercial and cultural relevance of 'nudie' magazines pales by comparison," he said.
However, the cultural relevance of Playboy was undoubtedly present four to five decades ago. The magazine has long offered more than just nude images to its readers.
"Back in the '60s and '70s, it was actually the bible for cool men's fashion. It was a way of understanding certain lifestyle that young men looked to live," Passikoff said. "The truth was that it became a platform for some phenomenal writers and artists."
Some experts speculate that the men's magazine might be slowly falling back on this trend in its upcoming redesign.
Thomas Ordahl, chief strategy officer at brand consultancy Landor told CNBC that Playboy is an example of a brand that can convert a historic style into a modern product.
"(Playboy) has enough awareness and traction and cultural relevance that it could be recast to be relevant in today's marketplace," Ordahl said on "Power Lunch" Tuesday. "They have the heritage, they have the very clear authentic position. It may be dated but that's a very strong place to start from than just zero."
Other analysts question if the return to fashion and lifestyle content will be enough to differentiate Playboy from competitors like GQ, Esquire or Maxim.
"It strikes me that if people were looking for a magazine that provided lifestyle and fashion tips for men, there are already established magazines out there," Passikoff said.
But Passikoff cautioned, "People shouldn't forget that Playboy has a digital presence on the Internet. It's not disappearing entirely.”
When Playboy did away with nudity on its website in 2014, the digital version actually attracted more traffic as well as a younger audience. Playboy told CNBC in May that this strategic decision resulted in a 375 percent increase in global unique monthly visitors to Playboy.com.
This leaves some industry experts wondering if this success will translate to the magazine, which isn't nearly as accessible to the younger demographic.
Passikoff said that Playboy ultimately needs to figure out who its audience is.
"The business problem is very clear," he added. "The question is, ‘Is this the right answer?’"