Joseph Rosenfeld, a downtown San Jose–based image consultant, says Silicon Valley’s relaxed approach to fashion came from the counterculture that evolved around the tech industry.
“It wasn’t really about ‘We’re so smart; we don’t need to be dressed up,'” Rosenfeld says. “It was really that the people who created a lot of what we know today to be the Silicon Valley, they were a little bit older and had left other parts of the business world behind. So they thought, ‘Hey, we’re going to be here, we’re going to relax our look a little bit, and it’s our right to be relaxed and be successful.'”
Rosenfeld, who claims to be the only certified male image professional in the United States, has been a fashion mentor for more than two decades. He says his clients are ardent about dressing down for work.
“Everyone that I work with in high tech tells me the same thing: ‘Oh, I don’t have to be dressed up at work, so try not to change me so much,” Rosenfeld says. “There’s an emphasis for them to really want to fit into the business counterculture style that technology companies have created that’s so pervasive. No matter what any of the rest of us do who aren’t in high tech, we’re all kind of enveloped in what that counterculture has done.”
In the early 2000s, khakis at the office were the norm, Rosenfeld says. Now, it’s all about the jeans.
“It’s like, I see those Rock & Republics, and you’ve got your 7s [For All Mankind] all over the place, and I have my William Rasts on today,” he says. “A lot of office dress-code policies are unwritten or are unenforced, so now, a lot of people’s offices are just in jeans, jeans, jeans all the time.”
Steve Jobs defines this casual tech-nerd aesthetic. No matter how many billions Jobs makes, his outfit remains the same: black long-sleeve mock turtleneck, relaxed fit jeans and tennis shoes.
“People always ask me about Steve Jobs and his signature look,” Rosenfeld says. “It’s like his uniform. I think what is crucial is, he can do it, but other people really shouldn’t because they haven’t reached his level,” Rosenfeld explains. “He doesn’t really have anything else to prove. A lot of other people are still looking to prove themselves to their bosses, to their co-workers, to their colleagues. I think this need to be viewed as a success gets lost in what we all call ‘business casual.'”
Rosenfeld says he thinks valley habitués seriously need to work on their style.
“I don’t even like the word ‘casual,'” he says. “I’m not trying to be a party pooper, it’s just we’re either not planning our looks, or we’re overthinking them in different settings.”
“I don’t understand why a businessperson, who really cares about their job, would think about their appearance in such a haphazard or a careless way. And even when it comes to making an impression on someone on a date, the same thing is true. If you’re going to the symphony at the California Theatre, you’d think you could sport it up more than putting on some jeans and a T-shirt. If you can spend a couple hundred bucks on a pair of premium jeans, you’d think you could do a little bit better.”
The Mild West
Joe Trdinich experienced style shock when he first moved to the West Coast. Back in 2004, he was a green engineer recruited right out of college by Microsoft. Having held internships at high-level tech companies in Manhattan and his hometown of Pittsburgh, Pa., Trdinich was stunned to see how causal work dress codes were more than 3,000 miles away.
“I still haven’t adjusted all the way, and I probably never will,” says Trdinich, now a 27-year-old software developer at Yahoo. He remembers sticking out like a sore thumb among the tech recruits when he went into his first Microsoft interview wearing a tie and slacks.
“I come from the East Coast, where shorts and sandals at work are just completely unheard of,” he says. “Here, it’s totally accepted and, I think, practically encouraged by the culture to dress overly casual.”
Like Rosenfeld, Trdinich does not approve. When he moved to downtown San Jose three years ago to work at Yahoo, the office-dress environment got even more relaxed, he says. Many tech companies encourage the blending of work and play, and include campus perks like basketball courts, gyms and lounges. Trdinich says most of his fellow tech employees are far more concerned with comfort than appearance.
Instead of the suits he wore every day in New York, he says his typical workday attire now consists of an ironed button-down shirt (no tie), designer jeans and nice leather shoes. He says that among his peer group at Yahoo, he has by far the most formal fashion sense. Nobody (except him, perhaps) would bat an eye if one of his fellow programmers rolled into the office in a tank top, flip-flops and cargo shorts.
Though the company policy of being unconcerned about looks helps keep the focus on the work at Yahoo, Trdinich does think something is lost by such a laissez-faire approach to office style.
“People feel they are judged very fairly based on the work they do. It doesn’t necessarily matter what you look like. It’s very much ‘What have you done?'” says Trdinich. “But, I guess I do think that leads to a general apathy about how you look, because people in the tech environment don’t think it really matters.”
Nevertheless, he is hopeful that tech-industry style will evolve.
“I think that 15 years ago it was certainly the nerdiest of the nerds were into this,” Trdinich says. “There certainly is that element still, but the software engineer is such a more widespread profession now than it was. You’ve got a much wider range of people that are going into jobs like software development.”
Hyperlocal Style
Silicon Valley fashion runs to the cliquey. Whether it’s upmarket spots like downtown Mountain View and Los Gatos, or more eclectic scenes like downtown San Jose, each neighborhood (or even bar for that matter) has its own look. Hit up Campbell or the coffeehouses around SJSU, and crowds tend to traffic in the “hipster” style of skinny pants, Vans, American Apparel hoodies and ironic glasses.
The Blank Club serves as de facto headquarters for San Jose’s retro-rockabilly scene, which bleeds over to places like the Caravan, Cinebar and other dive bars. Taking its aesthetic cues equally from punk-rockers and ’50s greasers, half-sleeve tats, chest pieces and pink hair are the norm. The pin-up Suicide Girl look is popular with the females, with many rocker chicks donning oversize flowers in their pompadoured, 1940s-styled hair. The overall look is retro, with a sexy twist achieved with of eyeliner, lipstick and oftentimes facial piercings.
The skater look remains popular with young male clubbers, all the better for moshing to the Shit Kickers or Whiskey Avengers. Guys in studded belts and pork-pie hats can be seen slamming back Pabst Blue Ribbon tall boys and Jameson’s.
Still, this self-defined rockabilly- style subculture overlaps the broader nightlife look.
Love it or hate it, downtown San Jose really does have an after-dark uniform: skin-tight black tube dresses and sky-high heels for the girls; spiked hair, embroidered or silk-screened button-up shirts; dark wash jeans and sneakers for the guys. This look flourishes at dance clubs like Sabor, Wet, Pearl, Motif and Fahrenheit. To many outsiders, it’s as though San Jose transforms on Friday night into the set of Jersey Shore. “I’ve had people make the comment, ‘Oh, let’s not go to downtown San Jose, it’s so ghetto,” Trdinich says, pointing out that many of his tech buddies prefer the posher scenes in downtown Mountain View or Santana Row.
Rosenfeld says he cringes sometimes when walking down the street at night near his condo at the Axis. “Being a downtowner, I see it all the time,” he says. “Women pour themselves into clothing that is so tightly fitted that you can see bulges of flesh and how the bra straps are so tightly bound through the back of their clothing. It’s like, ‘OK, honey, you’ve got it all on. But one false move, and it looks like everything is going to explode!”
“Showing it all off and letting it all out there for everyone on the street to see is not really that sexy,” he adds. “It’s really disturbing. I never want to insult anybody, but I always want to go and start handing out cards like ‘I can help you, I can help you.'”
Rosenfeld says that dropping hemlines slightly and wearing properly supportive foundation undergarments can make a world of difference in transforming a woman’s nightlife look from trashy to sexy.
The Row
If there is one place in Silicon Valley where people go primarily to see and be seen, it’s Santana Row. According to Rosenfeld, it’s where people really get dressed up and come to show off their style—or at least their pocketbook.
“If anyone doesn’t believe me,” he says, “all you have to do is see the fancy cars that you don’t see anywhere else in town, parked right outside the valet at the Hotel Valencia. If people are doing that there with their cars, they’re doing it with their style too.”
When he spends time at Santana Row, Trdinich has noticed it’s more common for people to put thought into their outfits. Even so, he says that the causal workplace look does spill over into a casual nightlife scene. “Santana Row is just people trying a little bit harder,” Trdinich says.
Flare
Rosenfeld says that the No. 1 thing people in the valley need to work on is their own sense of “flare.”
“We are like white bread compared to someone else’s pumpernickel or whole wheat,” he says of San Jose’s style. “I think that’s because if you walk down the street during the daytime, it’s just hard to find people who really have a great sense of flare. When you’re in any part of San Francisco, you can find people who have flare.”
Trdinich says he didn’t have a lot of money growing up. So, when he started pulling down a Yahoo paycheck and could afford stylish designer clothes, he had no idea where to start. Since hiring Rosenfeld as his image mentor, Trdinich says that he has become much more aware of how his sense of style affects both his office and dating life.
With Rosenfeld’s help, he says he’s chucked all his obnoxiously bright-colored T-shirts. He’s also become quality-conscious and learned that shoes really do matter to women.
Rosenfeld says that good style isn’t about brands but about people being willing to take a hard look at themselves in the mirror. Only then can they truly appreciate what’s special about themselves, which they can then show off through “flare.” “It’s not about socioeconomics,” Rosenfeld says of people with good style. “It’s that they’ve really put some degree of thought and care into themselves. They understand their own self-worth. They say, ‘I can put this on and rock it.’ I love that. Confidence is what you really end up seeing about someone, and that’s really attractive.”
