Elon Musk’s Fashion Evolution: From PayPal Nerd to Dark MAGA, Dressed for Launch

Texas, October 15, 2026. A red sports car drives up a ramp that curls over until the car hangs upside down, shoots off the end, rolls half a turn in the air and lands on its wheels. On stage, a man in black says: “Well, it worked.” The new Tesla Roadster was all over the internet within minutes. But it is not the only thing Elon Musk has been launching. For more than twenty five years he has been releasing a second product in ever new versions: himself. The packaging is his wardrobe.

Musk is probably the most photographed CEO on the planet. Line the photos up and you see a man who has changed his look about as often as Tesla has changed its delivery dates. Our video follows that story era by era. Here is the written version, and the question behind every outfit: what was it selling?

1999: a millionaire in a borrowed look

In 1999 a CNN crew filmed a 28 year old taking delivery of a McLaren F1, one of the most expensive cars in the world. He had just sold his first company, Zip2, to Compaq in a deal worth about $300 million, with his own share at around $22 million. His next venture, X.com, merged with Confinity in 2000 to become PayPal, which eBay bought in 2002 for $1.5 billion.

And the future billionaire’s style? Young engineer who grabbed whatever was clean: loose shirts, boxy jackets, nothing that said brand. Our reading: in the dotcom era, looking unstyled was almost a badge of honour. It said: I am too busy building things to think about clothes. It also said: nobody is designing this person yet.

The glow-up nobody confirmed

Over the 2000s, as Musk moved on to SpaceX and Tesla, his hair got fuller rather than thinner, and the internet has debated a transplant for years. Important: Musk has never confirmed one, and much of the detailed online analysis comes from hair clinics, which happen to sell the procedure. Treat any graft count you read with healthy suspicion.

What is clear is that the overall glow-up was real. Fitted jackets replaced boxy ones and dark colours replaced random ones. Musk started to look like someone who knew he was being watched, which made sense: rocket companies and electric car start-ups need investors and believers, and the founder becomes the face of the product. Silicon Valley already had its uniforms, Steve Jobs with the black turtleneck and Mark Zuckerberg with the grey hoodie. Musk chose neither.

Dressing like the future

He chose black. At Tesla launches Musk became known for dark bomber and leather jackets, black T-shirts, jeans and boots. At the 2019 Cybertruck reveal, an angular steel pickup straight out of a science fiction film met a CEO who looked like he came from the same set. Vogue compared the look to sci-fi costume design. Underneath came T-shirts with company logos and later memes, anime and gaming references, a style the fashion press labelled techwear minimalism.

On the red carpet, he tried other registers: at the 2018 Met Gala he wore a white tuxedo jacket with a collarless shirt. Our take: Musk understood something many CEOs miss. On launch day the founder is the product’s first accessory. If the car looks like the future, the man next to it cannot look like 2005.

Short shorts and slogan tees

Then Musk discovered that clothes can be jokes. In July 2020 Tesla began selling red satin shorts with gold trim and S3XY on the back, spelled out from Tesla model names, for $69.420. The number nodded to internet humour and to his 2018 tweet about taking Tesla private at $420 a share, which had cost him the chairman role. The target was obvious: short sellers betting on a falling share price. Musk literally sold them short shorts.

From then on the slogan T-shirt became a fixture: Occupy Mars, Tech Support, DOGE. These are not really T-shirts. They are tweets you can wear. A slogan on his chest gets photographed, shared and argued about, and the press release writes itself.

Black tie, leather armour and belt buckles

2022 was the year of the visible transformation. Musk was noticeably slimmer and, asked on Twitter how, replied “Fasting” and later added “And Wegovy.” In May, days after agreeing to buy Twitter, he climbed the Met Gala steps with his mother, the model Maye Musk. The theme was Gilded Glamour and he wore a black Tom Ford tuxedo, saying he was “basically dressed like I’m from Downton Abbey or something.” His mother added that he had bought it rather than borrowed it.

Six months later, at Heidi Klum’s Halloween party in New York, he went full fantasy in a black leather armour costume sold online as Devil’s Champion for around $7,500. And a new element crept into the wardrobe: Texas. With Tesla’s headquarters moved to Austin, Musk began wearing a large Tesla themed belt buckle, peacoats and boots. Part mid-century, part space cowboy.

Dark MAGA

Then the wardrobe went political. On October 5, 2024, Musk appeared at a Trump rally in Butler, Pennsylvania, in an Occupy Mars T-shirt and a black Make America Great Again cap instead of the classic red one, telling the crowd he was “dark MAGA.” According to Axios, as cited in an MSNBC column, the black cap brought in around $1.6 million in sales after the election, almost twice as much as the red version.

During his time leading the government cost cutting project DOGE, the Washington look stayed consistent: black cap, slogan tee, often no tie. At one cabinet meeting he paired a Tech Support T-shirt with a charcoal peacoat and his Tesla belt buckle. In March 2025 the Wall Street Journal spotted a Brioni jacket over a black DOGE T-shirt, dubbed the look Fancy MAGA and traced the dark aesthetic to online meme culture. At his Oval Office farewell on May 30, 2025 he wore all black, with a black eye he said came from asking his five year old son to punch him.

How you read these clothes depends on where you stand. Supporters see authenticity: a man who does not dress up for power. Critics see the opposite, and an MSNBC column described the casual look as a power move. Our take: both readings agree on one thing. These clothes were not accidental. In politics, as at product launches, Musk dresses for the photo. For another look at how executives use clothing, see our piece on Elizabeth Holmes and the black turtleneck.

The Roadster and the uniform

Which brings us back to Texas. Tesla first showed the new Roadster in 2017. Nine years later it arrived as a joint project with SpaceX, with compressed air thrusters, a ramp flip and a jump over a row of Teslas. Musk says production will start in 2028, while admitting that success “is not guaranteed”, and Tesla’s own website says the flying version is not approved for public roads. Critics call it a stunt, fans call it the future.

And here is the twist. The more spectacular the product, the less spectacular the outfit. When the car does a kickflip, the man can simply wear black. After twenty five years of costume changes, Musk’s most effective look may be the event itself. The lesson for everyone else: clothes can be press releases, a uniform can be a brand and when you are the most photographed CEO in the world, there is no such thing as just a T-shirt.