Before getting on with part two of my take on GQ‘s list of Silicon Valley’s worst dressed men, I must give them a shout out for having created it in the first place. It’s the gift that keeps on giving. If you thought my opinions from last week’s part one were strong, you’ll have to continue the journey as we move through the rest of the list here.

Silicon Valley's worst dressed menFrom my studio window overlooking downtown San Jose, I look directly at the Adobe buildings. Shantanu Narayen heads up the company, and maybe he should take a walk over and visit with me. He does another thing that many men in Silicon Valley do. He “powers down a suit.” But the look hardly comes across as “Chillaxed,” a hybrid attitude of being chilled out and relaxed. The shoulders are so broad on this jacket that they should have invisible speakers that yell “De-fense!” like a football cheer! The sleeves are clearly too long. They wrinkle up as he feigns the faux chillaxed look with hand in pocket.

The jeans go against everything I believe in as far as jeans go. You may even recall I just wrote about premium denim jeans two weeks ago, and these jeans are Silicon Valley's worst dressed mendefinitely not premium in any way. Really, Shantanu has a look that illustrates a lack of style and vision, when his company is all about both. I’m absolutely sure he has it, because he’s the CEO. But, it’s a wonder to me how and why he doesn’t convey it on behalf of his company. Call me Shantanu. I’m truly a block away from your office.

I’ve never even heard of Ben Huh, CEO of ICanHasCheezburger.com. So when I saw that he was listed, I said, Ben who? Maybe someone over at GQ knows more about him than me. But, a grown man wearing kitty cat T-shirts just can’t be taken too seriously. Whatever.

We always see Steve Jobs photographed while wearing the same black mock turtleneck, jeans, and sneakers. All ill-fitting – well maybe except for the sneakers – and all sloppy looking. He looks like a Palo Alto homeowner who wears black while doing yard work just because he can. Is that what he Silicon Valley's Worst Dressed Menthinks of the work he does at his beloved Apple? I’ve previously written about Jobs’ image in Metro Silicon Valley ‘Style’ columns. His place on the list is right on. Even the iPhone gets a makeover, but what about the Apple founder’s outfit? It’s well publicized that Jobs has been experiencing serious health issues, causing him to lose weight. But when you see him in this familiar set of clothes, it emphasizes his troubles.

Apple’s a very strong, resilient company. I think its nimble quality takes after its company founder. If he simply wore new and improved versions of his iconic uniform, he’d visually represent his full inner strength, and be a stronger visual representative of Apple.

Silicon Valley's worst dressed menFacebook’s Mark Zuckerberg topped GQ’s list, and although he changes his clothes, nothing seems to look like it belongs to him. With a borrowed fashion sense taken from clothes that look like he got them from a donation center, it’s no wonder that so many people see his appearance as a disgrace. I’ve posted about Zuckerberg’s lack of style before, too. My point essentially remains the same. There’s one great way that Mark Zuckerberg could ‘save face,’ and that would be to put some effort into developing a style that he defines, instead of allowing this shapeless style to visually define him. Personal style shows people where you’re headed, just as many people look to see where Zuckerberg is headed.

It would be a pleasure to work with any of the gentlemen on GQ‘s list of Silicon Valley’s worst dressed men, were they to call. But, I share my thoughts about these guys to point out that you don’t need to be famous to end up on someone’s “worst” list. With some effort, you can avoid being on such a list and even make it onto the “best” list. Yes, it’s great when people talk about you, and that when they no longer talk about you that’s when you should worry. But you know what? When people talk  about you because looking great, that sounds a helluva lot better than people talking about you for looking like a schlub.

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