CTRL+ALT+DEL: The 15 Worst-Dressed Men Of Silicon Valley
Photo: Getty Images1/1514. Craig Newmark
Position: Founder of Craigslist
Style Sins: To the surprise of no one, the guy who started Craigslist dresses like a guy who stalks Craigslist—wrinkled shirts, oversized blazers and a beret fetish (check his Twitter avatar, @craignewmark). There's a fine line between looking "artsy" and uncomfortable. Craig has stepped over it.
Photo: Getty Images2/1515. Chris Sacca (right)
**Position: **Founder and Principal of Lowercase Capital
Style Sins: While most guys would treat embroidered cowboy shirts like diseased cattle at the department store and walk on by, Chris Sacca hasn't met one he didn't want to snuggle. Now you know who's been snatching them up.
Photo: Charles Eshelman/Getty Images for AOL3/1513. Ron Conway (left)
Position: Early Investor in Google, PayPal, Facebook, Digg
Style Sins: No use telling this veteran angel investor to fire his tailor. It looks like he already did. Even as a heftier man, high water trousers aren't supposed to hover above your ankles, effectively cutting off your height, nor should blazers graze thighs. The effect can be penguin-ish.
Photo: © Randy Stewart, blog.stewtopia.com4/1510. Ben Huh
**Position: **CEO of ICanHasCheezburger.com
Style Sins: We get it. Your office chair is a FUF and you sift through zany cat pics for a living, hence the whimsical kitty graphic tees and white-rimmed specs. It's cute. But we can tell you just rolled out of your 1,000-thread count bed sheets and picked out the nearest T-shirt in or around the laundry basket.
Photo: Getty Images5/1512. Peter Chou
**Position: **Co-Founder and CEO of HTC
Style Sins: Much like angel investors and roughed-up dad sneakers, ill-fitting jeans are a recurring theme in Silicon Valley. Take that thing five sizes down.
Photo: Getty Images6/1511. Blake Krikorian
**Position: **Co-Founder and Former CEO of Sling Media
**Style Sins: **There's nothing wrong with dressing like every day is casual Friday. Copping a dress shirt in every Magic Eye pattern and jacking the IT guy's wardrobe, however, won't win you style points. Midnight Men in Black shades and dizzying striped button-ups sounds like a "Project Runway" challenge gone horribly awry.
Photo: Getty Images7/159. Howard Stringer
**Position: **Chairman, President and CEO of Sony Corp.
**Style Sins: **"Where's dad?"
"He went fishing."
"But there's no lake around."
"Well, he looked like he was going fishing."
Photo: Getty Images8/157. Tom Anderson
**Position: **Co-Founder of MySpace
Style Sins: Consider MySpace's most recognizable friendly face a victim of over-layering. Except in Antarctic temps, there's rarely a reason to wear a T-shirt, hoodie and blazer all at once, like Tom prefers. Even in the college-student-uniform department, Zuck has him beat.
Photo: Getty Images9/158. Seth Priebatsch
**Position: **Founder and CEO of Smartphone app SCVNGR
Style Sins: In addition to an unhealthy obsession with smartphones, Seth shares another trait with Steve Jobs: Great branding, bad style. With his signature ski goggles, sandals, "lucky" backpack, and shirts that bleed "Jersey Shore"-orange, the 22-year-old Princeton dropout must have better things to do with his life than shop. Like ski.
Photo: Getty Images10/156. Reid Hoffman
Position: Co-Founder and Chairman of LinkedIn; Investor in Digg, Flickr
**Style Sins: **Hoffman isn't Silicon Valley's most flagrant style offender, but it is easy to mistake him for the cable guy who shows up for appointments sometime between the hours of 8 a.m. and 9 p.m.
Photo: Getty Images11/155. Dennis Crowley
Position: Co-Founder and CEO of Foursquare; Co-Founder Of Dodgeball
Style Sins: After you've received your diploma and laid your butterfly chair to rest, all college sweatshirts and the like should be reserved for lazy Sundays, grocery runs, and gym visits. Unless Crowley is making a social statement about the threat of student loan debt, it's time to graduate past the junior section.
Photo: Getty Images12/154. Shantanu Narayen
**Position: **President and CEO of Adobe Systems, Inc.
Style Sins: You'd think the head honcho of the company that owns Photoshop would realize the importance of image. Practically swimming in his dad jeans, Narayen looks like Nate Robinson playing dress-up in a Shaq suit.
Photo: Kimihiro Hoshino/AFP/Getty Images13/152. Steve Jobs
Position: Co-Founder and CEO of Apple
Style Sins: Apple releases an iPhone every 0.5 seconds. Steve Jobs never gets an upgrade. The Svengali's self-inflicted uniform (black turtleneck, dad jeans, Seinfeld kicks) rival Superman's in its homogeneity—a style blunder no AutoCorrect can fix.
Photo: Matthew Staver/Bloomberg14/153. Bill Gates
**Position: **Co-Founder and CEO of Microsoft
**Style Sins: **Curious how Harry Potter will age post-Hogwarts? When you're Scrooge McDuck rich, a snazzy ensemble isn't tops on your to-do. Rather than swag out in Armani suits, Gates takes the lazy preppy approach, opting for a drawer full of V-necks in every hue. If only his proportions were on point, he'd look more like this, minus the body and athletic skills.
Photo: David Paul Morris/Bloomberg15/151. Mark Zuckerberg
Position: Co-Founder, President and CEO of Facebook
**Style Sins: **Oblivious to the fact that jeans and ties come in skinny sizes—or that suits exist—the father of Facebook (and we do mean father) loves to recycle the fresh-from-Stats-class look. Zuck's style is so poor, it even inspired a mock fashion line, Mark By Mark Zuckerberg, which thankfully doesn't sell any actual clothing.