I’ll never forget the first tech campus I visited back in 2018. In Palo Alto, California. I’d come for an interview at a senior engineering role and it was like walking into Stepford Wives: Everyone was wearing the same thing.
Grey hoodie. Dark jeans. Needless to say, those hideous Allbirds looking like chunky felt slipper socks your grandma knitted for you.
I was rocking dark jeans and my usual merino jumper – I felt overdressed. “You interviewing for management?” asked the woman at reception while staring at my jumper as if it had cooties. These basic black t-shirts proudly displayed by so many VCs and CEOs had long ago passed peak aspirational and landed squarely in post-peak cray cray territory.
Welcome to hoodie culture circa 2018.
Programming chicks ruled Mark Zuckerberg’s philosophy on wardrobing called “decision fatigue.” Why spend time, energy, or resources on how you look when there are better things to do? Think of Zuckerberg’s hoodie uniform as VC fundraising pissing contest of who could look more like Steve Jobs circa the 1990s. Investors wearing Amazon Alexa Cam-equipped black t-shirts was as bad as it got.
Fast forward three years. I just got back from visiting that very same company and… something has changed. Not everywhere – Google hasn’t pivoted to wearing Dockers just yet – but you can see the full employee spectrum out on many campuses now.
I met up with Marcus for coffee. He’s a product manager at one of those big name tech companies you’ve definitely heard of, even if you don’t use their product. Marcus wore Patagonia gadgetshirts so worn in they were basically giant holes with sleeves back when I met him four years ago.
Today, he’s still rocking what at a distance looks like a hoodie but is upon closer inspection clearly not a hoodie. It’s merino wool, cut much nicer than your average hoodie, zip-front, and most notably lacking a logo plastered across the chest. He’s wearing dark chinos that are suspiciously not khakis and white minimalist trainers that retail for more than some people’s monthly rent. “I got tired of blending in with every other dude,” Marcus said when I asked him about his outfit. “Girlfriend also said she was going to donate all my clothes to Goodwill while I was at work if I didn’t do something about it.” Marcus was the first of several people I met while visiting Bay Area companies last week who upgraded their tech wear.
During three separate company visits, I saw exactly five hoodies. Five. Everyone else was wearing t-shirts so well cut you’d think they paid for them to be tailored, Japanese oxford button ups with just enough texture to keep from playing it too safe, and yes, technical trousers.
But technical trousers that aren’t yoga trousers, and come from companies like Outlier that actually resemble trousers you’d normally wear in public, while somehow also being waterproof and stretchy enough to do yoga in. How did we get here? Well, the startup founders who built their companies in their mid-to-late 20s are now well into their 30s with new cars, mortgages, kids, and more disposable income than they’ve ever had in their lives.
Why spend it all on grilled cheese and video games when you can actually look like the successful entrepreneur you are every once in a while? I have yet to see an investor sign on dotted line on a $50 million deal while wearing sweatpants. COVID probably didn’t hurt the cause either.
When we were all remote working in our PJs 2020-2022, wearing a uniform became less about signaling to your fellow unicorns and more about existential dread. And once we all returned to offices, even if only a few days a week, many of us have been rethinking how we dress to work. “I texted you a month ago when I started randomly thinking about clothes,” said Jake, a software engineer whom I’ve known since college, over drinks last week. “Remember I said I needed help shopping? Ended up loving every thing you got me.
Learned I actually had plenty of style, I was just dressing like a college student who works at a tech company.” Jake ran wearing Dockers and an oxford through college. His entire office is now doing the same. It’s not just coders and PMs, either.
Chen, a UX designer at Meta who I visited with her team last Spring said it best: “I used to think putting effort into your clothes was superficial and bad for intellectuals,” Chen told me. “But I’ve realised it’s just design. We’re designers here, right? Of course we care about design!
So why shouldn’t we apply design thinking to what we wear?” The days of flashy California stars embroidered on backpacks are long gone. Now tech wear is about blending high-performance features with tried and true classic styles. Clothes aren’t simply basketball shorts and hoodie clones with fancier fibres.
Buttons are shiny. Trousers actually hug your hips instead of your childhood dreams. Fitted suddenly became sexy.
VCs and tech CEOs are rocking technical blazers from Ministry of Supply so stretchy you can deadlift in them. Wicking. Machine washable.
Waterproof. You can commute to work on your bike in these and they look legitimately sharp, not like someone’s dad who just got home from his real job. Which they pair nicely with those sweet performer cargo trousers that have been (finally!) replacing jeans as the de facto trousers of choice across Silicon Valley.
Esports decked out trainers are swapped out for premium white trainers from Common Projects or minimalist leather trainers from Koio that cost more than my first Macbook. Hell, even the “quip” backpacks that are now status symbols are from thoughtful design companies like Peak Design or Airport-ready Aer laptop bags that you’d be embarrassed to be caught with in Tokyo. And don’t even get me started on how far we’ve come with accessories.
Watches with numbers on them! Hats that aren’t ballcaps! “What’s most impressive to me?” I said to Chen. “How many quality garments people here are wearing that actually fit them.” She laughed, showing me off the sleeve of her Bluffworks dress she got me for my birthday last week. “Honestly, same,” Chen replied, pulling up the sleeve of her custom-fit Bluffworks dress I bought her for her birthday last week. I’ll never forget walking into Google headquarters a few weeks back, seeing employee after employee sporting crisp t-shirts from TNF’s new elevated basics line custom-printed with their company logo walking around Mountain View. “I’ve finally learned how to solve for clothes,” one Satya Nadella look-alike whisper-shouted to his friend while gesturing to his own tee. “Spent way too much time and money these past few years obsessing over it.
Couldn’t sleep at night knowing my wardrobe wasn’t ‘optimised’ enough.” It’s far from perfect. I see guys wearing Asics in Flip Flops in January. Old startup conference t-shirts that look like they’ll survive another five years.
Cargo shorts. I still see it. But I also see a very different conversations about dressing happening in tech than I did just three years ago.
Conversations about fit. Details. Tailoring.
Brands.
I saw guys and gals who looked like they knew what they were wearing and why they were wearing it. Who took intentional pride in their wardrobe.
Who took personal style as seriously as they took their job. Not an exaggeration. This was literally a photo Marcus text me from his company’s all-hands meeting last Friday. “The Slack poll is split 50/50 on who dresses better,” Marcus said. “Boss thinks I do, boss’s boss thinks he does.
I’m rooting for my team though.” Gone are the days of walking into a tech office and immediately knowing every employee’s job title based on their outfit. Silicon Valley has officially caught up to the rest of us. Ironically enough, most of it comes down to optimization.
Spend 30 seconds thinking about how you dress. Spend more than $30 on your clothes. Problems solve themselves.
Case in point, how Silicon Valley solved the problem of dressing.
