Vision Statement: Men’s Style in Silicon Valley … Or What Little There Is

Men's style in Silicon Valley: Our moguls dressing badly.

Your guide to men’s Style in Silicon Valley – From the richest VC to the masses of individual contributors, these guys need some help. Clockwise from top left: (1) Facebook’s Mark Zuckerberg; (2) Twitter’s Jack Dorsey (top second from left) is one of Silicon Valley’s few natty dressers. (3) The late Steve Job’s iconic black shirt, jeans and sneakers went from schlubby to hip through sheer force of personality; (4) Linked In’s Reid Hoffman; (5) James Gosling invented the Java programming language and men’s style in Silicon Valley as we know it; and  (5) Four Square’s James Crowley. 

Here’s what passes for men’s style in Silicon Valley

The Silicon Valley Engineer look is perhaps the most degenerate look there is for anyone allowed to come to work on a regular basis. Khaki shorts? Check. Faded T-Shirts? Check! Open-toed sandals with no socks? Double-check. Style? Gack. How about at least hiding your toenails from the world except when you’re at the beach? Is that too much to ask? Such is the state of men’s style in Silicon Valley. Or lack thereof.

I suppose it’s a case of “Oh, but I’m too smart to bother with such shallow pursuits as dressing appropriately – for anything!  I spend my time hacking Ruby and Javascript and I live on such a rarefied Platonic plane that looks simply don’t matter!  (Yeah, as if you were the only guy who knew how to do that!) I’m too busy holding my VP of engineering hostage with my exclusive database of knowledge to even think about it! Why should I care about how I look? Why does it matter, when folks will hire me without even a face-to-face interview?” Even compared to the (very rich) gentlemen in the figure above, some of the engineers I’ve met in my travels here come off far, far worse.

Are you too smart to care about it? Or too rich for it to matter?

Or maybe you’re too rich to care about men’s style, here, in the perpetual Gold Rush of Silicon Valley. The most aggressively obnoxious dressers tend to be the ones who have been longest at their companies. Especially when they’re sitting on so much stock-option wealth, at historically low capital-gains tax rates, that such sloppy dress amounts to an expression of power. This trend began during the 90’s dot-com boom and has taken root like Kudzu here. Along with tiny-wheeled $3000 folding bicycles and clandestine copies of the Wall Street Journal in their cubicles, the slobbo-programmer aesthetic is quite familiar once you’ve been here awhile.

Seriously, what does it say when absolutely everybody, even including the VCs and the top kicks at all of these places, all do exactly the same thing? While their $3000 Armani suits, which remain the only really nice clothes they have, sit in a closet? You never see these guys wear a tie, not even when their Fortune 500 customers come to call. Honestly, ties, fitted shirts and tailored slacks are still too much work for just about everyone. The more money you have, the more this becomes evident. I offer the following photo from Flickr as a stunning but by no means isolated example.

High Tech's 'best and brightest' giving Hillary Clinton a sad and sorry lesson on men's style in Silicon Valley. Too bad they don't look as good as the women.
High Tech’s ‘best and brightest’ giving Hillary Clinton a sad and sorry lesson on men’s style in Silicon Valley. Too bad they don’t look as good as the women. A HOCKEY shirt? A red track sweater?

The Double Standard

The aggressive assertion of frat-boy power in the pic above is absolutely evident. Now, it’s the women in the picture, one of whom you may recognize, that turn themselves out. The prevailing cultural attitude is; you’d better. But men’s style in Silicon Valley sets a double-standard for men and women. The man standing next to no less than the former Secretary of State, Hillary Clinton, is very, very rich. He is also very, very tasteless. Clinton and all of the other women in the above picture are turned out appropriately. But every single guy in the picture is wearing what I’d like to call their go-to-Hell outfits. One guy is wearing a hockey jersey – really? –  and appears to have expended a Herculean effort just to toss on a sport jacket. The fellow in the dark blazer appears to be wearing – jeans. It implies that Hillary should have been grateful they bothered to show up.

The women look great. The men look like – well, never mind.

A more aggressive assertion of power can rarely be found. Or a more transparently phony expression of rebellion. My God — I cannot imagine what I would do with my wardrobe if I had the cash these guys do. Half a dozen custom-tailored Armani suits would probably be a start. For my part, I would be horribly embarrassed or mortified to show up before the most powerful woman in this country dressed like that, whatever your political affiliation. It would be like showing up naked. It does not represent well and reflects badly on a number of psychological and political levels. John Waters’ quote says it all.

John Waters on Men’s Style in Silicon Valley and Elsewhere.

Men’s style in Silicon Valley — or lack thereof — has gotten go pervasive that even the anything-goes legendary cult filmmaker John Waters weighed in on the subject. Here’s what he told Put This On — which calls itself a “web series on dressing like a grownup” — back in July 2012:

“When I was young there were beatniks. Hippies. Punks. Gangsters. Now you’re a hacktivist. Which I would probably be if I was 20. Shuttin’ down MasterCard. But there’s no look to that lifestyle! Besides just wearing a bad outfit with bad posture. Has WikiLeaks caused a look? No! I’m mad about that. If your kid comes out of the bedroom and says he just shut down the government, it seems to me he should at least have an outfit for that.”

At the same time, some actual VC_funded services have shown up around here that attempt to consult the big wheels on how to do a better job representing. The next figure illustrates one poor fashion victim who wound up looking quite absurd. It combines an attempt to look more fashionable with the same hyper-casual aesthetic he appears to be trying to get away from. Capri jeans, anyone? This is what you wear on a fishing boat, not to the office. This was definitely the wrong Men’s Style consultant. (No, I’m not angling for the job!)

Man in white polo, schlubby jeans, and brown suede slippers
Victim of a bad fashion consultant.

Honestly, it doesn’t take gobs of money to do better. All you need to do is keep visiting this blog. You’ve got one life. Why not try to make the most of it by upgrading your look to match your circumstances? I’ll let you in on a secret – it’s also a lot of fun.

Men’s Style in Silicon Valley – this blog –  is a declaration of disagreement with the prevailing attitude towards representing yourself. I do not understand why hundreds of thousands of men who work in this cosmopolitan area, with ready access to one of the world’s great cities, and who almost uniformly make plenty of money, steadfastly refuse to make themselves presentable for such important things like dates, much less work, and as often as not wind up looking like colossal jerks. Over time, I will be posting images of guys I see pulling this kind of stunt. (Hint: Don’t wear a wife-beater, a basketball jersey or a weightlifting singlet on a DATE!!!!)

I am not talking about looking like a Wall Street shark or a stuffy white-shoe New York lawyer. What I’m talking about has to do with making people happy to see you, to avoid sending the wrong message to your interlocutors, to show others that you care about them to the extent that you will put yourself together to meet them. There also is a moral standard here that is manifestly ignored, particularly by the ruling classes in Silicon Valley, but also by their multitudes of tame technical savants, virtually all of whom inhale their Stanford-educated “betters’” ethos and attitudes like the finest Peruvian flake.

No, I am talking about expressing excellence as a man and engagement with the environment and those around you. With this fashion blog on men’s style in Silicon Valley, I hope to help guide men and assist their women in a movement to bring the Bay Area up to a better social, sartorial and intellectual standard. Looking good has everything to do with it. In Silicon Valley, looking good is a form of rebellion. Let’s get started.


About the author

Richard Grace is a technical writer and long-time denizen of Silicon Valley. He thinks men's style in Silicon Valley could use a bit of improvement. For the latest Groovy Man Stuff, friend him on facebook, "Like" his Groovy Man Stuff page, follow him on Twitter, or plus him on Google+. And since this is Silicon Valley, Richard also has a Linked In profile.