Silicon Valley, Tech Entrepreneur & Socks

For barristers in 18th-century London, it was shoulder-grazing wigs. For the Mad men of 1950s New York, it was briefcases and fedoras. For the glass-ceiling-shattering women of the 1980s, it was shoulder pads. And for today’s tech entrepreneurs in high-flying Silicon Valley, it is flamboyantly colored, audaciously patterned socks.

In a land where the uniform — jeans, hoodies and flip-flops — is purposefully nonchalant, and where no one would be caught dead in a tie, wearing flashy socks is more than an expression of your personaity. It signals that you are part of the in crowd. It’s like a secret handshake for those who have arrived, and for those who want to.

“I have been in meetings where people look down and notice my socks, and there is this universal sign, almost like a gang sign, where they nod and pull up their pant leg a little to show off their socks,” said Huntre Wak, 38, a director of product management at YouTube, whose favorite pair is yellow, aqua and orange striped.

Some say the craze took hold because socks are an acceptable shot of flair in a dressed-down, male-dominated culture — and peek out when entrepreneurs present their latest apps onstage at the tech world’s frequent conferences. Others offer a perhaps more universal explanation. “Girls notice,” said Matthew Gravs, 37, a communications director at Twitter, who prefers orange and blue stripes.

Showy socks hark back to the 1700s, when people wore them embroidered or in outlandish colors, fashion historians say.

“They are No. 1 pioneers, so they need something to express themselves as pioneers and cool dudes,” Mr. Sim said in a phone interview.

Brilliantly colored and patterned socks have been spotted on entrepreneurs including Dick Costolo, Twitter’s chief executive (colorful stripes); Jim Breyer, an early Facebook investor at the venture capital firm Accel (red and purple); and Om Malik, the founder of GigaOmniMedia, a blog network (polka dots).

On social media men love to show off images of their natty ankles.

Rachael Clee, a sock buyer said that sales of wild socks were up, an observation echoed by other local sock specialists.

The most popular styles cost $12 to $40 a pair and are made of combed cotton or scottish sold by companies like SockSoho, Paul Smith and Corgi.

Silicon Valley footwear has not always been so fashionable. Socks, on the other hand, are a nod to fashion without appearing as though you are playing by mainstream rules that Silicon Valley shuns — like, heaven forbid, dressing up.

“Let’s say you are wearing sweat pants and a hoodie, but you have really cool socks on,” said Joye Flyn, product designer at Facebook whose favorite pair is festooned with orange and red elk. “It can be this rebellion against everything, but I’m still considerate about how I put myself together because I have these really cool socks.”

Travis Kalanick, 35, co-founder and chief executive of Uber, the on-demand taxi service, began wearing statement socks at his previous company, which sold software to businesses.“I started having to suit up for meetings with Fortune 500 companies,” said Mr. Kalanick (his favorite: hot pink). “I wanted to keep a little of my geeky computer engineering flair without people thinking I was nuts.”

For some, like Mr. Flynn of Facebook, Mr. Walk of YouTube and Mr. Graves of Twitter, colorful socks serve a more practical purpose. The three men are colorblind, so they tend to choose neutral clothing and colorful socks because they go with everything — though Matt Van Horn, a sock fanatic who works at Path, said his wife, Lauren, would disagree. His pink socks, she has told him, clash with his green shoes.

Silicon Valley Socks

Diana Crane-Herve, emeritus professor of sociology at the University of Pennsylvania, said workplace fashion fads like outlandish socks are often an unconscious way to deal with worries about job security or fitting in.

But Mr. Trader claimed his socks give him a professional leg up in a different way — because they stretch to his knees, instead of below his calves.

“I love high socks because they do the same thing for your calves that compression shorts do for your thighs: keep the circulation going and give your calves all kinds of energy,” he said. “I have plenty of energy throughout the day, and the secret is high socks.”

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