Why tech billionaires keep changing their look

Alexandr Wang, 29, is not short of money. Meta, the company behind Facebook and Instagram, invested $14.3 billion in his company, Scale AI, to have him as its AI executive, Slate reports. Yet at Meta Connect in late September, the company’s annual event, he walked onto the stage in a camo T-shirt reading “Lake Tahoe”, black joggers, matching Crocs and a mullet. Someone online estimated the outfit at $3,500. Wang answered with an annotated photo: T-shirt, secondhand, $30. He even took care to specify the underwear, $5.

I found the story while browsing the Bluesky profile of Olivia Guest (she writes often about artificial intelligence and the study of the mind), whom I also recommend for gems like this one.

The thesis is that the heads of the big AI companies have discovered the appeal of looking harmless. The evidence is a list: Wang and the Crocs; Mark Zuckerberg, whose style changes arrive with Meta AI announcements; Palmer Luckey, who builds AI-guided drones for the Pentagon (the company is called Anduril) and walks around in a Hawaiian shirt. Note the kind of evidence: clothes and dates. The article admits that part of it may be taste changing with age, then says it is nonetheless “a conscious choice”. A choice, yes. A purpose, not demonstrated.

The script, besides, is messier than the headline. Wang goes toward the dishevelled, others went the other way. In July 2017, GeekWire described Jeff Bezos, Amazon’s founder, as “buff” at a media and technology gathering in Idaho. It noted that the change had been gradual and cited a 2013 observation by the writer Brad Stone: Bezos was by then training every day and, according to Stone, perhaps preparing for astronaut training. In that article, Bezos says nothing about training. In 2023, Charlie Warzel argued in The Atlantic (I ran a search with the machine) that Zuckerberg’s muscular image was deliberate, inspired by Elon Musk, Joe Rogan and Jordan Peterson, and not built to last. Indeed: today, Slate says, Zuckerberg goes around in oversized T-shirts with slogans, like “Building is my love language”. One man, three characters in three years. If it were a private healing, I’d expect one of them to stay. They look more like stage costumes.

I had my suspicion before all this. I remember my university classmates, the ones who swotted harder than anyone, full of complexes and with a big hunger for revenge. The revenge of the nerds, I wrote in my book, leaves me uneasy, and I say that as a nerd. And nerds are often thin-skinned. So I suspect that some of these men are building a body and a look in order to become, in their own eyes, someone else. Elon Musk, who runs Tesla and SpaceX, is not someone I like: I say so upfront, so you can discount it. Like many, I also suspect a hair transplant. As far as I could find, he has never confirmed it, so call it a suspicion and nothing more; it proves nothing about the why.

I’ll add an impression, and it remains an impression. I often notice a smugness in Bezos’s gaze since he put on the muscle, and in Musk’s when he wears his leather jacket, which looks straight out of a 1990s Schwarzenegger film. Much less when they have to squeeze into those sad jackets that people in the United States wear on formal occasions.

Executives fear becoming irrelevant, the old casual style hid insecurity, the new one is overcorrection, as an essay by Andrey Andonov argued in The Recursive, February 2025. His evidence is a screenwriting manual and a book on menswear: no statements from the people concerned. Against my suspicion: the character changes, Stone’s astronaut hypothesis, and the most obvious explanation, that at fifty people change how they dress and train. I’d need to hear them talk about themselves, and I haven’t found that. Until it arrives, “revenge” is an ingredient of my reading, not a conclusion.

One thing stands, whatever the reason. The costume asks something of us: it asks the public to read a body or a T-shirt instead of the product. And that matters, given what the products now do. According to Slate, Wang told the Connect audience he can follow individual users’ searches on Meta’s new personal assistant, with examples like the person who broke their mother-in-law’s favourite china set. I haven’t verified this. If it’s true, the question for a company asking for our trust is what its assistant sees and what it keeps. The $30 T-shirt is a way of not making us think about that question.

For what it’s worth, I judge an assistant by what it knows about me, not by its Crocs.