Hoodie, early-stage startup tee, bright-colored sneakers, jeans: This is the uniform of an aspiring millionaire in Silicon Valley.
Tech workers have long been derided for their terrible fashion sense — even if their signature “I don’t care” look is by design. In an industry obsessed with frugality, utilitarianism, and efficiency, dressing down is a badge of pride.
But things are starting to change: Thrust into the public eye, tech execs are increasingly turning to personal stylists to overhaul their image — and sometimes, their entire personal brand.
Where fashion came to die
During the 1980s tech boom, cultural norms of all variety were thrown out the Window(s)™.
At companies like Apple, Atari, and Sun Microsystems, employees came into work at noon and left at 2AM. They brought their dogs to work. They wore their hair in greasy ponytails. And they shunned traditional dress codes: Suits were abandoned for business casual; business casual gave way to t-shirts and “econo-brand sneakers.”
This carefully-manicured “efficiency over appearance” ethos has carried on through the years, fueled by some of tech’s most prominent leaders.
In the vein of Steve Jobs, Mark Zuckerberg wears the same thing every day: A gray t-shirt and jeans. “I really want to clear my life to make it so that I have to make as few decisions as possible,” he said of his closet, in 2014.
Zuck’s minimalist look isn’t merely an act of efficiency — it’s a call to the world that he’s a man of the people, a man of the coders, true to his roots. It’s also, at least in part, a carefully crafted act: His t-shirts are custom-made in Italy and run $295 a pop.
“It’s a cliché that tech workers don’t care about what they wear,” wrote venture capitalist Peter Thiel in Zero To One. “Everybody from slackers to yuppies carefully ‘curates’ their outward appearance.”
But this “I don’t care” trend is fading
In recent years, tech execs have been unwittingly thrust into the public spotlight.
They’re no longer behind the scenes refactoring lines of code: They’re testifying in Washington, giving speeches at international banquets, and gracing the covers of magazines. The public scrutinizes their every move.
As Paul Kedrosky, of SK Ventures, told Marketplace, we’re in the age of the “celebrity tech CEO.” Suddenly, execs — many of whom are ex-coders with no prior background in business (and often, no fashion sense) — are in a position where they have to be taken seriously by the broader general public. They start with their wardrobe.
Look no further than Jeff Bezos, who, between 1998 and 2017, managed to pivot from a slouching sweater enthusiast to a Vin Diesel body double in a power vest. Or Elon Musk, who went from a balding coder in a purple button-up to a perfectly-coifed, leather-jacket-wearing alpha male.
When Zuckerberg testified before Congress earlier this year, many on the Hill seemed more concerned about his wardrobe than the Cambridge Analytica data breach itself.
“Is he going to wear a suit and clean white shirt?” President Trump’s chief economic advisor, Larry Kudlow, asked the press the day before the hearing. “That’s my biggest question: Is he going to behave like an adult, as a major corporate leader, or give me this phony-baloney — what is it? — hoodies and dungarees?”
The suit, posited the The New York Times, signified Zuck’s metamorphosis. “[It] was a growing up moment,” wrote the paper. “The suit is the costume of the grown-up, while the T-shirt is the costume of the teenager, the off-duty, the breaker of rules.”
Tech execs are begrudgingly accepting this — and they’re shedding their hoodies for a brave new world of style.
The hoodie exterminator
As a personal stylist rooted in Silicon Valley for 25 years, Victoria Hitchcock has witnessed the shifting tides of “tech fashion” firsthand.
After stints as a runway model and a tech marketer, she decided to pursue a career as a style consultant. With a $5k loan from her sisters, she launched Victoria Hitchcock Style in the late ‘90s, at the height of the Dot-Com boom.
Today, her clients include tech execs at Apple, Google, Uber, Microsoft, and IBM. As she told Vox, her role is to help them “go from boys to men.”
The process is kind of like the (now discontinued) television show What Not to Wear. It begins with a Skype consultation, in which Hitchcock gets to know her client (his/her lifestyle and schedule; what he/she does for fun; why he/she is looking to for a change, etc.). Then, there is a “wardrobe edit.”
“I’ll go through his closet and basically filter out the bad stuff,” she says. “And we’ll start from the ground up.”
Some of the more common “mistakes” she sees in tech workers’ closets: old, over-stretched jeans, moccasin slippers (worn as everyday shoes), Crocs, and khakis (which she says “nobody should ever wear”).
“Denim is one of the most blatant offenses,” says Hitchcock. “Some of these guys think it’s okay to keep a pair of jeans for 4 or 5 years. It loses its shape over time, and it’s a completely different fit by then.”
Techies are also extremely particular about their socks. “Seriously,” she laughs, “I hear so much about socks: Too thick, too thin, too high, too low… They struggle with socks.”
Once the offending items are filtered out, Hitchcock accompanies her client on shopping trips, pointing out things to look for based on the client’s tastes and lifestyle. For her services, she charges an initial consult fee of ~$2k; after that, it’s $275 per hour.
Higher-end clients often opt to keep her on retainer, at a rate of $10k per year.
A whole new person
In the age-obsessed Valley, where the median worker is a mere 29 years old, Hitchcock attracts aging tech execs who are having aesthetic identity crises.
“Tech workers in their 40s are caught between two worlds,” she says: “They want respect from the 20-something coders they manage, but also need to be taken seriously in meetings with VCs and foreign backers.” (Turns out, Chinese investors in $5k suits are not impressed with the ol’ t-shirt and jeans ensemble.)
Henry*, a 37-year-old CTO at a mid-sized tech startup, recently found himself in this position. He was “one of those [old] dudes in a bright blue hoodie and flip-flops,” and didn’t really care since he was hanging around a bunch of coder subordinates all day.
During a burst of press, Henry decided to consult with a stylist: In short order, his hoodie was swapped for a cashmere sweater, his faded jeans were upgraded to commuter chinos, and he bought his first pair of oxfords, a welcome replacement for his 6-year-old New Balance 574s.
For execs like Henry, Hitchcock suggests “camera-ready” clothing that allows for easy transitions during 16-hour days.
“I’ve been with clients through the entire journey from starting their company, to selling, to entering the public eye,” she says. “My role isn’t to give them a business uniform; it’s to help them optimize performance.”
Tech execs often want to overhaul not just their style, but their entire personal brand.
Hitchcock goes beyond the role of a traditional stylist and into the realm of life coach, doling out advice on everything from buying yachts to finding love. She works with plastic surgeons, dentists, skin care professionals, hair stylists, and fitness trainers to bring Prince Charmings out from underneath their hoodies.
“Sometimes,” she says, “it really is like looking at a whole new person.”
Fashion tips for the tech lifestyle
Hitchcock offers several tips for tech execs (and office workers in general), who want to maintain a nonchalant look in a more put-together way.
- Shoes: Low top Converse, slip-on Vans, black lace-up shoes, Chelsea boots
- Tops: Lightweight sweaters, shirts in checkered patterns, shearling coats, long leather jackets
- Bottoms: Tailored pants, one pair of “go to hell” pants (bright, audacious color)
- Accessories: A sleek backpack (Tumi Arrivé)
- General tip: Avoid matching more than one article of clothing
- Shoes: Kitten heel pumps, short booties on pointier side (in neutrals)
- Tops: A knee-length overcoat
- Bottoms: Long pencil skirts
- Dresses: Go flowy, with long sleeves (prints in peacock greens and blues)
- Accessories: Crossbody bags with golden metallic chain
- General tips: Choose perfumes that are “less sweet and more mysterious;” use a hydrating gel for night
There is, of course, an exception to these rules: If your name is Jeff Bezos, you can wear whatever the f*ck you want.
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