It looks like Microsoft is trying to make key executives look younger and cooler with new clothes and haircuts. This is certainly one way to try and unseat the iPhone and PlayStation among college kids.

The latest makeover appears to be Joe Belfiore, VP of the Windows Phone Program. Today he unveiled a Windows 7 smartphone that needs to be cooler than the iPhone, a tough sell for a company that makes most of its money selling distinctly uncool word processors, spreadsheets and operating systems to old people.

But as Engadget’s pictures prove, Belfiore’s clothes and hair certainly sent the right message, especially when compared with his headshot on his official Microsoft profile. See picture above (click to enlarge). (The phone itself is apparently pretty nice too.)

Microsoft appears to have employed a similar strategy when selling videogames, another market dominated by young trendsetters. Chief Experience Officer J. Allard oversees Xbox and the Zune, and was once content to appear in official photos with a bald spot, button-down shirt and jeans. Now it’s a bald head, stubble, and either a hoodie or t-shirt. Below, find his old official picture (top left), new official picture (top right), Allard in hoodie with jacket (Getty Images) and Allard in a pinstripe hoodie (by Derek K. Miller on Flickr). Click to enlarge.

Microsoft’s makeovers are just the latest evidence that technology companies are increasingly enmeshed into the worlds of entertainment, media, design and even fashion. Steve Jobs’s decade-old uniform of jeans, sneakers and black turtlenecks used to reinforce his status as his industry’s leading cross pollinator, the man who turned Pixar into a powerhouse film studio and signed record and TV execs into the first blockbuster online media store. Now Microsoft is trying to take it to the next level, and has clearly moved past Jobs’ Gap outfits in fashion terms.

On the other hand, we know some other Silicon Valley execs whose fashion cred gives the ‘Softies a run for their money. Keep trying, guys. If anyone sees any other remodeled tech honchos, do let us know about it.

(Hat tip to the other Gawker Media editor who tipped me off to this.)

View full post on Gawker: valleywag