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How to dress tech bro
Charting the evolution of Silicon Valley style
© Getty Images. Amazon founder/CEO Jeff Bezos
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Hannah Murphy MARCH 13 2020
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As the old adage goes, you don’t know what you’ve
got until it’s gone. And it’s true – I didn’t realise
how much I appreciated style until it had all but
disappeared. Last January, I said goodbye to
London in all its sartorial diversity and headed to
the West Coast to write about technology. Here, I
was greeted by a de facto male uniform of bland Tshirts, ill-fitting jeans, oversized hoodies and
sneakers or, even worse, flip-flops.
This basic garb, sported by timid nerds and rowdy
tech bros alike, has been the staple of Silicon Valley
style. From the heady heights of the dotcom boom
to today’s techlash, the mantra has been simple: no
plain, no gain. It is easy to pin the aesthetic – or
lack thereof – on laziness: an absence of creativity,
regard and time. But the tech titans have, in fact,
been assiduous about dressing to a kind of casual
uniform.
The late Steve Jobs © Getty Images
The godfather of Silicon Valley style was,
undoubtedly, Steve Jobs. Through the late 1990s
and early 2000s, the tech pioneer would unveil the
latest Apple product in a black mock turtleneck –
made by Issey Miyake, no less – paired with blue
501 Levi’s jeans. He reportedly told his biographer
Walter Isaacson that he had “hundreds” of
black turtlenecks – “enough to last the rest of my
life”. This carefully curated branding helped
perpetuate the idea of the genius founder; droves
of young engineers were able to pay homage to the
billionaire they aspired to be by donning identical
get-up (though some copycats were perhaps less
flattering than others – see corporate villain and
ex-Theranos chief executive Elizabeth Holmes).
Hackett wool-blend gilet, £295 © Pixelate
“[Silicon Valley types typically] honour the style of
their champion. It’s part of a herd mentality,” says
Joseph Rosenfeld, a personal stylist who has
worked with clients in the tech sector.
There are a smattering of San Franciscoheadquartered brands that have cashed in on such
mimicry: sneakers from Allbirds – makers of “the
world’s most comfortable shoes” – and Everlanes
abound. E-commerce ventures such as Stitch Fix
allow overworked geeks to subscribe to receive a
curated package of clothing each month without
having to leave their hot desks.
Snapchat CEO Evan Spiegel © Getty Images
Twitter founder/CEO Jack Dorsey © Jeff Gilbert/Shutterstock
But the ultimate symbol of Silicon Valley’s herd
mentality is the zip-up vest or gilet. The look, once
associated with blue-collar workers, was
popularised several years ago as the regalia for the
elite Allen & Company Sun Valley Conference in
Idaho, also dubbed the “summer camp for
billionaires”. So ubiquitous is the style now – most
notably Patagonia’s fleece iteration – that it has
spread to the finance bros of New York and even
earned its own viral Instagram page:
@midtownuniform.
The dogma is that minimalism and monotony yield
extra productivity. “I really want to clear my life to
make it so that I have to make as few decisions as
possible about anything except how to best serve
this community,” Mark Zuckerberg declared in
2014 when asked about his single- shade-of-grey
wardrobe. It is startup culture flipping the bird to
corporate norms; a newfound promise of
meritocracy based purely on how well you
program, rather than present.
Mark Zuckerberg © Getty Images
Zuckerberg has set the tone for the Valley more
than anyone else. The social-media mogul was a
mere college kid in grungy teen outfits when he
started the platform. His statement since has been
to never outwardly change. On stage at the Web
2.0 summit in 2007, he unashamedly wore
black Adidas sliders. When the company floated in
2012, he rattled Wall Street financiers by wearing
hoodies to meetings. At Facebook’s developer
conference last year, he chose a highly
unremarkable blue-grey sweatshirt, black-jeans
and black-trainers combo. “It’s much more about
stealth wealth than anything. It’s not really about
showing off,” says Rosenfeld.
But the tide appears to be turning, signalling a
mild onset of “decision fatigue” fatigue. As tech
founders mature and grow alongside their
companies, many are honing a more unique image,
according to Silicon Valley fashion-stylist Victoria
Hitchcock. “The sweatshirt is a symbol of the anticonformist. It says, ‘You need the value of what I
offer. I’ll put my feet up on the desk, I’ll wear my
dirtiest jeans…’ It was about being comfortable and
not changing for anybody,” Hitchcock says. “But
the minute it becomes a uniform, it’s lost its
purpose. That’s the irony.”
So too have they turned to designers. The tech bros
of today wear hoodies and sweatshirts by Loro
Piana or Brunello Cucinelli, often with price tags in
the thousands. Lanvin sneakers are a hot ticket
among tech execs, as are those from Golden Goose
and Common Projects. Twitter CEO Jack Dorsey
favours Rick Owens jersey knits. Snapchat CEO
Evan Spiegel wears sleek, bomber-style jackets, as
does Google CEO Sundar Pichai.
This more fashion-forward mentality has been
driven by new business and social opportunities.
The bookish Jeff Bezos, who
launched Amazon from his garage, once wore
oversized khaki trousers and blue linen shirts. But
it is a different Jeff Bezos – in tight-fitting Cucinelli
T-shirts and Crime Scene Investigator aviators –
who is now rubbing shoulders with Hollywood’s
film and television elite as he expands his business
to include a media empire. “You better have a new
way of interacting with these people that isn’t
California casual,” Hitchcock says. “It’s not going
to fly.”
Even that cornerstone of Silicon Valley style – the
gilet – has had a high-fashion update in recent
years: execs have upgraded to slick sleeveless
puffers from the likes of Moncler and Herno.
Yet despite this veer towards more fashion-forward
choices, one thing remains consistent: Silicon
Valley is full of followers. “I was known as ‘the
hoodie exterminator’, now I’m ‘the vest
exterminator’ too,” Hitchcock says, in reference to
the once-sneered-at, now-ubiquitous gilet. While
the area may be a hub of innovation – the home of
unicorns – it’s hard to code individual style.
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