Elon Musk's Cringey Cowboy Throwback Pic Confirms What Everyone Already Knew

Elon Musk has given the world many things, like Musk's business ventures; he owns a range of companies, including X (formerly known as Twitter), SpaceX, and Tesla. On the non-business side, the CEO has also given us some awkward dance moves, and Musk was Donald Trump's most embarrassing sidekick at CPAC when he wielded a chainsaw and wore dark sunglasses with a large chain necklace. All that cringe is apparently nothing new. Musk shared a photo of himself on X, seemingly as a teenager, wearing a ball cap on top of a cowboy hat, wielding a hammer, and wearing capri cut jeans.

Some commenters on the pic were baffled as to why Musk had shared the photo at all. One critic commented, "Imagine posting this of yourself and thinking it's not the cringiest thing ever." Another said, "Not the flex you think it is, Cosplay Cowboy."

The first "America's Next Top Model" winner Adrianne Curry posted about it, summing it up for many by saying, "this entire photo is FULL of WTF." For all his money, and Musk is the wealthiest person in the world, Musk can't outrun the cringe, and at this point, he might just be leaning into it.

Elon Musk shared the awkward photo after he'd been seen in a cabinet meeting with Donald Trump donning a red "Gulf of America" hat without taking off the black DOGE hat that he already had on. Each of the attendees had a "Gulf of America" hat in front of them; Musk was the only one who put it on and was the only one already wearing a hat. Noting the hat-on-hat look, Trump said, "Elon, I love the double hat by the way. He's the only one that can do that and get away with it" (via The White House). Musk replied, "Well, Mr. President, you know they say I wear a lot of hats. And as you can see, it's true. Even my hat has a hat." He got some polite chuckles.

This cringey moment tracks, both for the odd hat situation and the attempt at a joke. One Trump administration insider told Rolling Stone: "I have been in the same room with Elon, and he always tries to be funny. And he's not funny. Like, at all. He makes these jokes and little asides and smiles and then looks almost hurt if you don't lap up his humor."

Musk seems to have a thing for inexplicable hats. He was also pictured wearing an oversized red MAGA hat in the Oval Office in February 2025. That was before the public breakdown of Trump and Musk's relationship. There was also the time that Musk was seen apparently wearing a cowboy hat backwards. While there were some who say he had it on the right way, it's still one of Musk's outfits that missed the mark.