Can you Algorithm-ise Cool? Why Tech Bros are Taking Over Fashion

Fashion has always been about cultural and social influence. But can you buy your way in, or do you have to earn it? The nerds and geeks who once rocked hoodies with flip flops have given up their anti-fashion uniforms and pivoted to hype-tier sneakers and front row invitations to Milan fashion week. These guys aren’t generally known for their fashion sense, but it looks like they’re heading into their rebrand era.

For years, dressing down was like an unspoken Silicon Valley law, with the exception of Steve Jobs who was known for his black turtlenecks courtesy of Issey Miyake. In the original tech culture that favored T-shirts and jeans, caring about clothing seemed like an afterthought tinged with a tiny bit of disdain. Being concerned about what you wore was for people who didn’t have bigger, world-altering things to worry about. But it seems the tech dudes have changed their minds, and I think the reasons behind that are worth digging into.

It’s interesting that the big tech bros at the top who I’d call elder millennials, born roughly 1981-1985 like Mark Zuckerberg, have become the poster-children for this pivot. These middle-aged men with billions of dollars must finally feel like they’ve cracked the code to cool, with their Patek Philippe watches and silver chains. It’s interesting that these guys, who sit somewhere in their early-40s, even care about what they wear, when they previously didn’t at all. Now that they’ve successfully disrupted tech, why are they making fashion their next target?

There’s likely a few reasons. One is personal branding, trying to seem like an aspirational-yet-relatable figure in an uncertain world. The other possibility is that these men grew up in a very specific cultural moment that has probably shaped their self-confidence. As adults, they want to have it all. They want to be successful and they really* *want to be liked. In the 1990s and 2000s, what you wore signified who you are, sorting people into a hierarchy of social status much more than clothing does today. Watch an early 2000s teen movie makeover sequence, especially the part where the weird kid gets reinvented, and you’ll see what I mean.

That’s why the progression of dorky tech men into their new fashion-adjacent iterations feels so strangely loaded. It’s like a remnant of clique-culture from their childhoods. Now, I’m by no means a therapist, but I do know about how clothes can change what others think of you and how you feel about yourself. What we wear is always doing a job, whether we want it to or not, and our clothes are inherently a statement about who we are, what we value, and how we move through the world. Perhaps more importantly, these tech figureheads probably know that they need to address waning public sentiment towards their industry, and they’re tapping fashion for the identity makeover they think money can buy. Zuck and his friends didn’t just wake up one morning and decide they care about clothes. I think they’re too calculated for that to be all it is.

They’re trying to do to fashion what they’ve done to tech - algorithm-ise it and optimise it for their own purposes. But releasing a chore coat, rocking up to the Met Gala, and getting outfit inspo from Instagram isn’t going to magically solve the public opinion problems tech is facing. After swathes of layoffs and an unpredictable future with AI, there is no amount of money or a magical fashion algorithm that will engineer likability and trust. Being respected and widely loved, with a solid identity and personal brand, doesn’t wholly come from the clothes you wear. It comes from the person wearing them.