Last week, GQ Magazine published its list of the Silicon Valley’s 15 worst dressed men. You go GQ! To be fair, several of the techies listed do not even physically reside in SV. Just the fact that GQ singles out SV as a style influencer proves a point I made in an earlier post rebutting Marc Andreessen’s attitude about the way tech company founders dress. In it, I said, “the world looks to Silicon Valley, not just to see what the next innovation will be, but to see what will become of our apparent lack of style.”
So, let’s zoom in on the Silicon Valley “Style Sinners” who GQ feels could use some polishing in the image department.
Chris Sacca, Founder and Principal of Lowercase Capital, has studied and lived in various parts of the world. It’s sensible that his personal style would be influenced by that kind of life experience. But when you look at the selection of embroidered cowboy shirts that GQ calls him out on, they don’t flatter him any more than his bed head hairstyle. Surely he’s got such an affinity for this kind of look that he’s even having these shirts made. The least he could do is choose colors that enhance his appearance. But he could go a step further and allow his style to mature, using what he has liked about western wear and embroidery as positive influences so that he looks modern, sophisticated, and sharp-minded, instead of looking like a tumbleweed in a cowboy shirt.
Craig Newmark, Mr. Craigslist himself, looks like a caricature, a goofy cross between that of a French painter and of the now deceased Dom DeLuise. Now, I have no idea how this kind of look developed, but it didn’t do him any favors. The notion of a fuller figured fellow wearing garments that actually accentuate his girth is what pulls my eye’s attention, as much as it pulls at the shirt’s taut fabric. Craig, you and I could do so much better together. Look for my listing on your site!
Ron Conway, an early investor in companies like Google, PayPal, and Facebook, made the list because of his apparent lack of tailoring. Truth be told, the angel investor must not have an angel as a tailor, that’s for sure! But whoever has been helping rich Ron select his clothes hasn’t been helping him either. The jacket length is too long. It’s a problem from right off the rack. A garment that looks like this clearly could not have been made-to-measure, unless it was fit for another human being. Check out the coat’s sleeve length. It’s also too long. A suit coat’s sleeve length is intended to be longer. But this is a sport coat, and the sleeve length should be shorter. Worn with wrinkled khakis that are too short, and with shoes that a nun may covet, Conway’s entire outfit strikes three sins of a bad dresser. Conway lives to give life to tech companies worthy of success. There’s hope for this angel investor’s style if he’s up for the challenge.
Then there’s Blake Kirkorian, Co-Founder and former CEO of Sling Media. I call him the average SV looking guy, which is why he must have made the list. Why, you say? Because his style is symbolic of all that’s boringly wrong with the way SV guys dress. It’s formulaic, but the formula is a fashion disaster. How cliché has it become to roll up buttoned long sleeves to give an air of “je ne sais quoi?” My question is really [French] tongue in cheek because the phrase really means, “I don’t know what,” and I don’t know what the hell that look actually conveys in a positive light! It’s sloppy. He’s hiding behind sinister glasses. He looks like he should be coming over to repair my computer and charging a lot of money to fuel his obsession with chardonnay. But other than that, I can’t identify with a redeeming quality about this sort of style. Get some new shirts, Blake. Get some jeans that flatter. Wear some sunglasses that don’t wear you. Tuck in your shirts. And look me up for some good old-fashioned guidance to help you look fresh and updated.
Reid Hoffman is the man behind LinkedIn, the social media site everyone tends to agree is the social space for professionals. It’s the site in which so many people go out of their way to post a well-posed photo in order to make a positive first online impression, or remain visually anonymous. Knowing that this is the premise of LinkedIn makes this image of its Co-Founder perplexing. Clearly this does not reflect a good image for such an influential man in Silicon Valley. GQ says he looks like a cable TV guy, and I’ve got to agree! You can be any size, have any body shape, and look like a formidable player, though I honestly don’t think Mr. Hoffman looks healthy for his age. Don’t let yourself go, Reid. Look for my ad on your site and call me. You’re a major player, not a guy who plays with cables.
Visit the blog next week, for part two, including the CEO of Adobe and the co-founders of Apple, and Facebook. You don’t want to miss a word.
Joseph Rosenfeld helps high-profile individuals revitalize, manage, and be secure in their personal visual brand. Visit JosephRosenfeld.com for details.
