In 1996, before Silicon Valley geek went C-suite chic, Netscape co-founder and future VC king Marc Andreessen earned what was then the ultimate business establishment honor: the cover of Time magazine. The story described the internet-browser wizard as a new kind of millionaire visionary. Yes, Netscape's recent IPO made the 24-year-old fabulously wealthy overnight, but he claimed not to care about money. After all, he still lived in a rented two-bedroom house and spent all his money on CDs and dog toys.

Before you even read the article, however, the photo of Andreessen already conveyed all you needed to know about his particularity: There, in all of his casually disheveled glory, was the young founder sitting on a plush, red-velvet throne in jeans, a wrinkled black pullover, and shoeless feet as pale and naked as the day he was born.

At the time, Andreessen's toe show caused a tidal wave of tut-tutting and eye-rolling from traditional business types. Who was this baby-faced clown and why did he look like he'd been collared by a Time photographer outside of a Phish concert?

But Andreessen was playing his own canny game of footsie, sending unshod semaphore to the world that he was a carefree non-conformist--so busy thinking Deep Digital Thoughts that he didn't have a moment to waste on petty concerns like, you know, shoes.

Twenty five years later, Andreessen's shoeless gambit--and don't think for a second that it wasn't a gambit--has snowballed into one of the strangest phenomena of the internet age: the "candid" barefoot CEO photo. These days, you can't call yourself an outside-the-box tech titan without photographic proof of naked tootsies for Wall Street Journal subscribers to ponder.

Herewith is a rundown of some of the more high-profile, post-Andreessen examples of this unbelievably bizarre business trend:

Mark Zuckerberg

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Everyone knows that the Facebook founder loves a hoodie. It's been his signature look since the early days of the social media giant. But at 37, with a net worth of $126 billion, Zuckerberg can't quite pull off the whole shoeless enfant terrible act with the same street-cred--even if his creepy wax likeness at Madame Tussauds in San Francisco features him in bare feet. On Zuck, it feels extra forced. We get it, you're a different kind of capitalist. (But, are you really?) Now, go put on some flip flops.

Mark Cuban

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When he's in the Shark Tank, Cuban favors suits and crisp dress shirts. Sitting courtside at Dallas Mavericks games, he's usually in a T-shirt and jeans. But outside of those settings--say, chilling in the Mavs' locker room, studying the latest white paper, or just generally taking a break from some light billionairing--the early tech founder likes to let his feet flag fly. It's not a pretty sight. His unspoken message seems to be: "I'll give you $100k for 51 percent of your company right now if you pretend you can't smell anything."

Richard Branson

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Before he rocketed into space, the rule-breaking English magnate with the leonine mane always came off as one of the coolest and most casual billionaires in the world. Not only does he have his own airline and space exploration company, but he also owns his own Caribbean island, Necker Island, where he no doubt takes long walks with the sand dancing through his toes. Going shoeless is just part of the whole Branson La Dolce Vita. Still, unless we're your guests on Necker Island, no one's dying to see your hooves. That kind of thing may float in space--but then again, in space, no one can hear you scream.

Chris Hotchkiss

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The CaptureRX co-founder has been called a "resurrected hippie" and "the Barefoot CEO" in the press. He also claims to be intensely private. But apparently not so private that he wouldn't pose for photographers with his au natural feet kicked up on his desk as if to say, "Sure, I may run a hugely successful healthcare admin company, but check out how chill I am!" In case the point wasn't made clearly enough, Hotchkiss also made sure to roll up his shirtsleeves to offer a peek of his badass tattooed forearms. "Hey, Wall Street--welcome to the gun show!"

Elon Musk

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Of course, Elon Musk can't be bothered with such earthly humanoid concerns as shoes. Or maybe he's taking the whole carbon footprint thing too literally. Recently, Richard Branson (natch!) posted a photo of himself with a barefoot Musk. (Branson, inexplicably, wore shoes.) In short order, the photo was uploaded to the foot fetishist archives "wikiFeet," where toe aficionados were less than impressed. Musk's dogs received a mere 2.7 rating out of 5. Ouch!

Adam Neumann

Hours before being forced to step down as the CEO of WeWork, the shaggy haired Neumann was spotted walking down a Manhattan street chatting away on his cell phone in jeans, a gray T-shirt, and filthy bare feet. This may be normal behavior on the West Coast, but in New York City?! Where every square foot of sidewalk is stained by dog poop, human waste, and good old-fashioned toxic gravy? Hasn't this guy ever heard of Tetanus? Then again, seeming footloose and sneaker free appears to have been the point. As the details of Neumann's executive demise were being negotiated, the founder's lack of footwear tried desperately to signal the time-worn mantra: What, me worry? Maybe you wouldn't sweat the small stuff too hard either if you were on the receiving end of a $445 million exit package.